Jon Plummer

There are lots of great articles about developing a roadmap for a product or service. But sometimes these processes can seem too heavy, too slow, or too strategic (is there such a thing?) for the task at hand. A lightweight process, aimed at selecting and ordering improvements rather than expressing an ideal and working toward it, can work when certain conditions are met.

Conditions

1. The product (or process or service) exists already.
2. Stakeholders are certain the product does essentially what it is supposed to do, but are dissatisfied by the results.
3. There are too many potential problems and potential fixes to clean them all up in a single project, though this is desired, or
4. the political situation is such among stakeholders that choosing a good place to start will be difficult (some may not want their area touched, others may want to go first, still others may not want to work.

These conditions assume that the strategy is good, and that the stakeholders’ attempts to fulfill that strategy are based on sound choices, but are perhaps not well-executed.

Goals

To successfully produce a roadmap and manage the political situation among the stakeholders we must accomplish a few things:

1. Uncover and arrange opportunities for improving the product.
2. Group and sequence the opportunities.
3. Plan the work for the first step on the roadmap.

Along the way we must be careful to:

• Make good use of any work the stakeholders have done to date.
• Demonstrate to stakeholders that we understand the current situation.
• involve the stakeholders in determining the value and feasibility of addressing each opportunity.
• Involve the stakeholders in negotiating the roadmap and selecting the first step.

Stakeholders appear in each of the four points above. We must bring them though this process and ensure that they are heard, and are at times active participants, but we must not become wrapped up in their shenanigans. There are defined points in the process where we involve them.

The process

1. Investigation

The first few steps of the investigation phase will occur together, and as you learn more you may find yourself returning to stakeholders for clarification, more information, or scope adjustment. The investigation phase typically takes the longest of the three.

1. Stakeholder research to establish goals and wishes, and collect their ideas.
2. Primary user and stakeholder research to understand existing needs and processes and learn of opportunities
3. Review secondary research (research done by others).
4. Express any found problems/opportunities (often pain points) in terms of their benefits (“gain points”) and likely features.
5. Arrange these opportunities by theme to see if and where problems are concentrated.

Step four is critical: you’ll have detected many problems and pain points, but need to express them first in terms of a benefit you’d like to deliver rather that just a feature. Remember that a benefit is the result of having a problem solved expressed without regard to the exact method of solving it. If you learn that students struggle to fill out a financial aid form on time, it would be tempting to offer an advisor to help them. That’s a feature, and it might not be the right one; the benefit may be that students have the information they need to fill out the form quickly and submit it easily. Go ahead and offer features, but only after identifying the benefits. The stakeholders will help us choose features once the benefits are clear.

We arrange opportunities by theme now to see if it tempts the stakeholders to narrow the scope of the project. You have to start somewhere, and the earlier we can reduce scope the higher the likelihood that the project will produce a useful first increment.

At this point you’ll have be ready to show the stakeholders your understanding of the current situation and the opportunities you’ve uncovered. This will fulfill both “make good use of any work the stakeholders have done to date” and “demonstrate to stakeholders that we understand the current situation” reminders above.

2. Synthesis

You’ve produced the raw material necessary for the stakeholders to help arrange opportunities into a rough sequence. Depending on scope the entire synthesis phase could be done in one workshop, or it might require two with some thinking and preparation in between.

1. Have a workshop with stakeholders to score opportunities by value and feasibility.
2. Examine the high-value, high-feasibility opportunities for common themes, then sequence all opportunities within these themes according to value and feasibility. More doable and higher-value items come first, and valuable low-feasibility items come last.
3. Have a workshop with stakeholders to arrange these themes in sequence according to feasibility and value.

Scoring opportunities for value and feasibility is a simple matter of placing these on everyone’s favorite business diagram, the 2×2 matrix. Items in the high-value, high-feasibility quadrant are potential good places to start. You’ll want a small but politically-effective number of stakeholders in this meeting; too many and it will be hard for the group to make decisions. too few and they won’t be informed enough to make good decisions.

This process requires you and the stakeholders to discuss how each of the opportunities might be met; what improvement (feature or change) would deliver the desired benefit. So we are sneakily involving the knowledgeable stakeholders in choosing improvements to deliver the benefits. They will feel useful pressure to help come up with high-feasibility ways to address high-value items.

Some items will be high-feasibility but low-value. These are nice-to haves that probably should not appear in the ultimate roadmap. Put them in a parking lot so that no one need be sad about them being cut outright. Still others are both low-feasibility and low-value. The stakeholders might have pet items among these. They should also go to the parking lot unless great ideas come up about how to rethink them, their value and feasibility jumps as a result, and the prior research supports their inclusion.

The themes that emerge from looking at the high-value, high-feasibility items are more informative than the rough themes we offered in the investigation phase, and will govern the arrangement of opportunities in the roadmap. And when you look at them you will likely see that some of these themes contain more high scoring items than others.

Offer these themes and the improvements they contain to the stakeholders in a workshop, and ask them to put these themes in order. If we could work on just one theme, which theme would we choose? That one will be first. By the end of the workshop you’ll have themes in a rough sequence, and within these their opportunities in a rough sequence.

You could stop here, but it is likely that the stakeholders aren’t done yet.

3. Negotiation

Now that you have a sequence of themes, and within those a sequence of improvements, you have a roadmap. But it puts some lower-feasibility items ahead of others just because of the themes they appear in. It also may offer a sequence that is awkward to accomplish, or doesn’t begin addressing top organizational goals early enough. Time for negotiation.

1. In a workshop with stakeholders, negotiate tradeoffs in improvement sequencing to better meet organizational goals.
2. Once that negotiation is complete, in that same workshop select one or a few items earliest in the sequence to make up the initial project.
3. Then go away and plan and estimate the cost in time and treasure to effect that project.

If you have the right small group of stakeholders, they’ll notice that they can rearrange some items to have the roadmap better address systems, efficiency, or political factors, start delivering against key goals sooner, or have certain improvements essentially make decisions early that will be helpful when tackling later improvements. Let them make these tradeoffs. The integrity of the themes is not important; we used the themes as a tool to make the rough sequence easier to accomplish.

After the tradeoffs are done, look to the items at the early end of the roadmap for the scope of the first project. It is tempting to bite off too much; everyone is excited about all the things you’re planning to do together. It’s best to keep the scope of the first increment small, achievable, not too expensive. Short projects with narrow scopes are more likely to succeed, after all.

Why not define an ideal?

You’ll note that this process does not define an ideal end state nor attempt to arrange a roadmap to produce that end state. End-state-based design is interesting (and there’s a very nice process called Ideality that depends on an understanding of the ideal), but I’ve elected not to make use of it here. There are several reasons for this.

• Producing an expression of an ideal end state, when there are lots of potential improvements, is expensive.
• The sequence of roadmap items aimed at an end state is likely to be different than a value- and feasibility-weighted roadmap which leads to high value improvements more quickly.
• Understanding and acceptance of an ideal end state tends to decay rapidly as business conditions change and new information and technology becomes available.
• Commitment to an end state reduces optionality, the ability of the organization to make new decisions about the future as needed.

Instead, this roadmapping process relies on the improvements themselves and especially benefits they are intended to deliver to take the place of an ideal end-state. These benefits express the desirable future in a diffuse, less-specific manner. Indeed, the later and less-feasible an item on the roadmap the less likely it is to be developed. this is true fo end-state-based roadmapping as well; the likelihood that the organization will pursue the entire roadmap diminishes over time. Why not embrace this constraint?

I contacted seven recruiters I had recently communicated with by whatever means we had spoken before. Most of them wanted to take the discussion to phone or a video chat, but for scheduling reasons I had to steer the discussion to email. Two were confused, one didn’t respond, and four said things that were helpful.

Three types of recruiters

My respondents agreed on three types of recruiters and their differences:

1. Contingency recruiter – this recruiter gets paid a percentage of the your first-year base salary upon hire. It’s a numbers game: most of the candidates they offer to companies don’t pan out, so they have to rapidly evaluate and offer a lot of companies a lot of candidates to make their time pay off. These recruiters have the least knowledge of the hiring company and the role, and may not even have a contractual relationship with the target company. They have little influence on the target company’s decision and do the lest legwork to make sure there’s a good fit. You can find a job with the help of a contingency recruiter, but they are helping the company only minimally and want to get you to an interview as fast as possible, not as well as possible. They specialize in individual contributor or low-level managerial roles, where the numbers of applications and opportunities are both high. Their tools are primarily keyword searches on large recruiting platforms such as LinkedIn, Indeed, Glassdoor, etc. This recruiter consumes job ads posted by companies and in-house recruiters. A solid LinkedIn profile that discusses the right keywords, and a resume that mirrors, it are keys to success with this group.
2. In-house recruiter – this recruiter is paid a salary by the hiring company, or is a contractor for them, and works solely on that one company’s behalf. They typically know the hiring manager and have worked with the hiring manager to refine their own evaluation of candidates. They may look at portfolios if they feel comfortable, and will read more deeply into a candidates profile so that they can filter more carefully and reflect that they have done this work to the hiring manager. They exert a little more influence in the hiring process, and work on positions at any level up to and including middle management. This recruiter posts job ads, sometimes in specialized locations. They do keyword searches to sweep up a lot of profiles, then comb through these to create a smaller volume of potential fits for the role. A solid LinkedIn profile that discusses the right results, and a resume that mirrors it, plus some evidence of the same in a portfolio, are keys to success with this group.
3. Retained search recruiter, sometimes known as “executive search” – this recruiter is paid up-front to fill an important position, and if they are doing their job well will have a relationship with the hiring manager, understand much more about the company and the position, and will be working from a “spec” that is much more detailed than a job description. The hiring company may have told them to favor candidates who have worked at similar companies, competitors, or places that are doing work that the company wants to do. They often understand team dynamics and the political situation at the company that the candidate would become part of. As a result they must do much more up-front assessment, understanding the profile and portfolio and doing much more in-depth screening interviews before offering a candidate to the hiring manager. They are a true gatekeeper in the process. This recruiter typically does not post job ads. The ability to do fine in a basic interview without warning, plus a resume and portfolio that display the necessary skills and acumen, are essential to success with this group.

You can tell what sort of recruiter you are dealing with in part by the level of information they provide and their ability to answer questions. If they can’t say much more than you can read from the job description, or deflect questions about the role with a “that’s a great question for the hiring manager,” you’re dealing with a contingency recruiter. It’s up to you to look at the company and decide if you’d like them to send your profile to the hiring manager. If you are approached by the recruiter they could be in-house or retained. If there’s no job ad and they interview you while telling you about the position, they are likely retained.

To be fair, all recruiters will try to qualify you, will try to make sure you are articulate and interested in the right things, are open to the salary and duties the company is offering, and are willing to take the next step in the process. But they will spend different amounts of time on that, and that time scales directly with how helpful they are to the hiring manager and to you.

My assumptions

My respondents also agreed with some of my assumptions:

• I assumed that a hiring manager who is not a product person will be seeking to add or improve the design function in their organization by hiring a seasoned leader who can evaluate current staff and processes, develop staff, hire, improve processes, improve integration of the design function with the rest of the business, bring new capabilities to the design function, and deliver results in doing so that clearly further the aims of the business.

This was unanimously supported.

• I assumed that a hiring manager who is a product person will have goals for the improvement of the design function, but will not be able to accomplish it on their own due to too many people and/or product lines to support, rapid growth, expertise or interest gaps, or other structural challenges. They may have a strong sense of the signals they are looking for, but regardless of that will be helped by clarity that I can tick all the boxes as a design leader.

This was unanimously supported.

My respondents were not in unanimous agreement about other assumptions:

• I assumed that a recruiter is going to try to match my profile to the “spec” they are given, either a job description or something more specific about the signals the hiring manager is looking for. So a recruiter will be looking for these signals in my resume, and possibly in my portfolio. They are not likely to be expert in experience design, so the recruiter will be watching for general quality of portfolio items and that the right topics are mentioned or otherwise evident.

I learned that successful retained search recruiters will have more expertise in the role of the target, and some in-house recruiters, especially for large firms, also specialize. These people will evaluate portfolios with a critical eye and set aside candidates that don’t seem to have relevant experience, much as a hiring manager doing their own recruiting would. In addition, retained and in-house recruiters will also be looking for credibility in the treatment of topics such as design thinking, design systems, and process. Portfolios that demonstrate these are seen as more valuable even if the general quality of work is less-well understood by an individual recruiter.

• I assumed that whether a recruiter is the first hurdle or not, the needs of the different types of hiring manager will be essentially the same.

In smaller organizations the hiring manager may do their own recruiting, and will have less patience to go through many profiles in depth. You’re likely to be quickly rejected if your fitness as a candidate isn’t immediately apparent. As the hiring manager rises in the ranks of a hiring company, the importance of each hire increases but their ability to spend a lot of time on recruiting falls, making it increasingly important that profiles advanced by the recruiter are high quality. So the interesting difference is less the hiring managers’ needs (all hiring managers need quality applicants) and more the level of assistance they are given (or can afford).

For me

I also asked these recruiters about my own profile. They found the following items important:

• Experience with hardware and software
• Experience managing cross-functional teams
• Evidence of design thinking
• Roadmap or other work to inform or assist product management
• Evidence of process – this was fine but there could be more
• Direct-to-consumer work – one recruiter felt this was lacking, which probably means I didn’t portray the audiences adequately
• Evidence of design systems – this was lacking somewhat
• Evidence of design workshops – this was lacking somewhat
• Client-facing work – this was lacking

I note that none of the recruiters mentioned other joys of mine, such as developing design talent, integrating research into company decision-making, mentorship of designers and managers, or harnessing existing data sources to improve products. I could usefully make more of these points. I should not write a lot more in portfolio pieces or resume entries to try to fill in these gaps; every word should do hard work, especially in these settings. Too much prose won’t be read at all. So I’ll need to find other ways to accomplish this.

Expectations of myself

• Foster an ethos of continuous improvement
• Repeatedly return to user needs and goals to create alignment
• Frame design goals as the marriage of user goals and business wishes
• Exhibit genuine care for each person I support
• Use wisdom and humor when shaping behavior
• Model desired behavior and attitudes for others
• Address what’s needed wherever it appears

Expectations of designers

• Scenario-based, goal-oriented
• Use storyboards to start understanding a scenario
• Freely move between storyboard, workflow, wires, prototype as needed to tackle problems
• Make small prototypes to test and learn
• The prioritization and arrangement of data directs user attention and action
• Organize “done” work into bite-size chunks, set apart from exploratory work

Expectations of all workers

• Work to make the job of the next person easier
• Work in public, out in the open
• Go and see
• Be aware of and have your work informed by user goals and business needs together
• Create possibilities cheaply, winnow according to goals, improve the best ones
• Involve others in solving problems, chewing on possibilities
• When presenting possibilities, arrive with your own evaluation of each one – pros and cons, fit to purpose, what you like and don’t like – and the sort of feedback you need
• Scope is negotiated – watch for improvements AND for lighter interventions
• Experiment with possible improvements to your own and collective work

Recruiters I’ve recently spoken to about passive opportunities (where the recruiter reached out to me before I was aware of the position) are more accessible to me than hiring managers, so my research will have to start there. In a previous article I said

The first step in capturing passive opportunities is clearly to get my profile in front of relevant recruiters. LinkedIn seems pretty good for this. While my LinkedIn profile is also not a subject of this research, I’m sure I’ll learn things relevant to it along the was as well.

The second is to get that recruiter to invite me to an interview so I can get them to pass me to the hiring manager if the position seems to be a fit. My impression is that my resume does an okay job here, and my portfolio could do better. I don’t know how many good opportunities have not com my way due to insufficiency of my portfolio, and I’m not sure I have a way of finding out.

The third is for my profile and the assessment of the recruiter to work together to encourage the hiring manager to grant me an interview. My impression is that my portfolio is not effective in this third step.

Revamping my design portfolio: audiences

The questions raised here include

• Is LinkedIn a good way to get my profile in front of recruiters?
• Does my resume do a good job of getting the recruiter to pass my profile on to the hiring manager?
• Does my portfolio do a good job of getting the recruiter to pass my profile on to the hiring manager?

But of course these are not the sorts of questions I can usefully ask directly; the likely answers (yes or no) wouldn’t improve my understanding much or help me make changes. Instead, I should ask questions that will help me gauge the effectiveness of what I have, provide details that may lead me toward changes, and identify what is already working. These questions will look more like

• Which of my assumptions are off base? (with a list of these assumptions)
• For the position in question, did you have any misgivings about my profile, other than location?
• What seemed most relevant about my profile?
• What seemed to be missing?
• Did you review my portfolio?

This sort of question will ideally not be too much to answer, and spark a little conversation that will help me know what to keep or play up in my profile, what to give more emphasis, and where I’ve left gaps. But first I must get them to engage, so I’ll contact them via LinkedIn with a simple message:

Hi, [name]. I’ve decided to turn my design research powers on my portfolio and resume. I’d love to ask you a few questions, since we recently discussed a position. If you are willing, I promise to make it easy and not take up too much of your time. Yes? Thanks, —Jon

Next up: understanding the results.

In a previous post I said

My highest-level goal is to be an impressive candidate design leader to firms that are looking for experience design leadership. They needn’t work hard to qualify themselves; I’ll assess these companies myself for culture, personal growth opportunity, financial opportunity, and interesting work to do.

Revamping my design leadership portfolio: goals

I’d like my portfolio to represent me well for advertised positions that I apply to, and for positions where a recruiter comes to me as a passive candidate. These two avenues probably have different processes and slightly different audiences. I’m a little bit more interested in the passive opportunities, since recently these have been the more interesting ones (iRobot, Neato, Kohler), but I suspect that there will be goals enough in common that I can do a good job for each audience with one portfolio. (For now I’m going to leave my resume out of the analysis and research, though I am sure I will learn things that are useful to improving it along the way.)

Since I have some experience recruiting designers and managers in small and large companies, I understand that the key variables and audiences break down like so:

• When applying to an advertised position, one’s profile is screened
  • first by a recruiter, then passed to a hiring manager for further review, OR
  • first by a hiring manager who is a “product person” (knowledgeable about experience design or product management), OR
  • first by a hiring manager who is not a product person (focused on some other area such as engineering, sales, or marketing and less knowledgeable about experience design or product management).
• A passive candidate’s profile is first screened by a recruiter, then
  • reviewed by a hiring manager who is a product person, OR
  • reviewed by a hiring manager who is not a product person.

The first step in capturing passive opportunities is clearly to get my profile in front of relevant recruiters. LinkedIn seems pretty good for this. While my LinkedIn profile is also not a subject of this research, I’m sure I’ll learn things relevant to it along the was as well.

The second is to get that recruiter to invite me to an interview so I can get them to pass me to the hiring manager if the position seems to be a fit. My impression is that my resume does an okay job here, and my portfolio could do better. I don’t know how many good opportunities have not come my way due to insufficiency of my portfolio, and I’m not sure I have a way of finding out.

The third is for my profile and the assessment of the recruiter to work together to encourage the hiring manager to grant me an interview. My impression is that my portfolio is not effective in this third step.

I’m going to have to make some more assumptions here, but my strategy should not be informed solely by assumptions.

Assumption: a recruiter is going to try to match my profile to the “spec” they are given, either a job description or something more specific about the signals the hiring manager is looking for. So a recruiter will be looking for these signals in my resume, and possibly in my portfolio. They are not likely to be expert in experience design, so the recruiter will be watching for general quality of portfolio items and that the right topics are mentioned or otherwise evident. I’d like to test this assumption, learn if it is correct and how I might address it.

Assumption: a hiring manager who is not a product person will be seeking to add or improve the design function in their organization by hiring a seasoned leader who can evaluate current staff and processes, develop staff, hire, improve processes, improve integration of the design function with the rest of the business, bring new capabilities to the design function, and deliver results in doing so that clearly further the aims of the business. I’d like to test this assumption.

Assumption: a hiring manager who is a product person will have goals for the improvement of the design function, but will not be able to accomplish it on their own, due to too many people and/or product lines to support, rapid growth, expertise or interest gaps, or other structural challenges. They may have a strong sense of the signals they are looking for, but regardless of that will be helped by clarity that I can tick all the boxes as a design leader. I’d like to test this assumption.

Assumption: whether a recruiter is the first hurdle or not, the needs of the different types of hiring manager will be the same. This assumption feels pretty safe, if the above hypotheses hold.

So, how might I test my assumptions for each of the three audiences? What might my research plan be for these three audiences?

Often in design research we look where the light is best. Folks like to complain about this; it’s a bad way to look for your keys, for example. But needs must; we may not have direct access to the people we need to learn from. In this case, I do not have direct access to hiring managers of either type that I have recently succeeded or failed with, other than my current boss. I do have access to the recruiters I’ve spoken to recently. I can start with them.

These recruiters are busy people, so I’ll need to interrogate them gently and in ways that don’t feel expensive to them in terms of time or thought. But I can send an email asking if they’d be willing to answer a few questions by email about the recruiting process and my case in particular, and see what they say.

Next up: the message and the results.

A little while ago I resolved to use explicit dimensions to solicit peer feedback and to organize my feedback on employees I needed to review. I also said that I’d let you know how it goes.

Quality – HMT (how might they) contribute to better results for the users of the product/project

Content – HMT improve the delivery of their own work

Collaboration – HMT foster greater collaboration among the team

Client – HMT better serve the needs of the client

Improvement – where have we noticed improvement in the review period

My previous post: Reviews

I’ve done two such reviews this way so far, incorporating these dimensions into the existing structure.

Peer feedback quality was greatly improved. Not everyone had something to say for each dimension, but when they did it was more useful and a nice mix of specific praise and specific constructive feedback. And the recipients of the feedback noticed and appreciated this difference. Granted, the prior peer feedback solicitation questions were pretty slim, essentially “do you have any constructive feedback for {person}” and “do you have any other feedback for {person}?” So anything might be better.

In each review I’ve gone over the peer feedback and my own thoughts for each dimension, and brought key points for praise and development in the summary. Employees have found this helpful, and the specificity (both topic and feedback) sparked good discussion. Granted, without the usual tight connection of the review to compensation there was less pressure on the employee’s part to maneuver the discussion toward whatever would get them the biggest raise. We were free to talk about the future, informed by the past, rather than be tempted to merely put the bravest face we could on the past.

There’s an opportunity to reinforce team or company values, or other desired behaviors, with review dimensions such as these. As we hammer out which behaviors these are, I expect the dimensions will change. For now I’ll go on using them as-is, as they have already been bearing fruit.

I’m not in a big hurry to leave my job (hi, folks!). But every once in a while a really nice opportunity comes along, and I’d like to be prepared for it. And of late I’ve felt that I’m not prepared. I think my portfolio doesn’t reflect my value as a design leader; it’s only a little bit past a designer portfolio, and a hastily thrown-together one at that. Sure, it was sufficient to get my current gig, but I fell into the lap of this company at JUST the right moment; a lot of this last transition is down to good luck.

This is a good reminder that you should be looking for your next job before you want your next job.

Roy Rapoport, Director of Corporate Engineering at Netflix

Recently we’ve started to revamp the company site, which has gone untouched for half a decade. In doing so we’ve selected two audiences we want to impress based on our business goals, done research on each, and penned some aims and a mission for the site based on that research and some hopefully reasonable assumptions when research didn’t suffice.

I’ll take a similar approach, at least conceptually, to improve my own portfolio, using my own goals (why have a portfolio site, after all?) and what I’ve learned in my many contacts with recruiters and hiring managers over the past few years. Over several posts I’ll go through the process, and eventually arrive at a portfolio site that I am proud of and I expect will do the job.

My highest-level goal is to be an impressive candidate design leader to firms that are looking for experience design leadership. They needn’t work hard to qualify themselves; I’ll assess these companies myself for culture, personal growth opportunity, financial opportunity, and interesting work to do.

My design leadership portfolio will contribute to that goal by suggesting to recruiters and hiring managers looking for a product design leader at the director level or better that I am worth further evaluation and an interview.

It’ll do so by demonstrating that my teams make great experiences for normal people in software, hardware, out-of-box, and services.

It’ll do so by showing how my organization of the team, the process, and the work, and my wrangling of the particular challenges of each project, contributed to outstanding results.

It’ll do so by reflecting how I lead teams to use research, usability testing, and metrics to produce good experiences and improve them over time, and where organizational failure to do these things left money and opportunities on the table.

It’ll do so by making it clear that I’m concerned with exactly the things that a growing business needs to pay attention to, including

• delivering delight,
• becoming recommendable,
• demonstrating thoughtfulness through meaningful differentiation,
• avoiding churn, cancellations, returns, and support costs, and
• demonstrating continuous improvement.

Further, it’ll do so by demonstrating that mentoring and developing designers, writers, researchers, and accessibility specialists is a part of the job that I find important, enjoy, and am successful at.

These writings have a part to play, of course. My ability to explain concepts, reveal my thinking, and work in public are all facets of my work personality that are material to whatever success I’ve had so far. So it’ll be a help if these sometimes refer to the portfolio and vice versa.

Equally important are non-goals:

• While I know a bit about HTML, CSS, and JavaScript, and cut my teeth on CSS back when we were rebuilding table-based layouts without tables, it’s not important that I showcase particular skill with these tools. So I don’t need to shy away from tools that make producing a site easier. I don’t need to hand-roll everything.
• While I’m a design leader, I’m not producing a lot of shipping design myself; rather I’m helping teams of people think about and organize their work, and developing those people and the processes in which they operate, to deliver excellent experiences that drive business results. So I need just enough polish to demonstrate thoughtfulness and get my points across. I don’t need to create a truly bespoke design. The content will matter more, and team results will matter more, than the frame in which these are shown.
• I’ve learned that designer-manager positions often become one or the other to the dissatisfaction of everyone. I know that what I love is coaching, up and down, and I don’t want a player-coach role. So while my own design aptitude is important, my individual work should take a back seat to the results I lead cross-functional teams to achieve. My own sketches to help foster that achievement may have a role to play, however.

So I’ll need to select projects and produce case studies that provide opportunities to do these things, and be explicit in pointing these things out as I go.

Along the way I’d like to do things a little differently. I’d like to share credit, perhaps by naming people who played a special role on the team. I’d like to discuss the sort of culture I hope to foster on design teams, where the team makes decisions together, knowingly for the good of users and the business, and sign-off by a superior is neither necessary nor sought. And I’d like to set myself up for regular maintenance of the portfolio, such that it’s not burdensome to add to it over time. I’d rather not go through a spasm of intense work as I have at each major job transition in the past; rather I’d like a small amount of continuous effort to result in my preparedness for these transitions when the opportunity arises.

What’s next? I can see a handful of needed activities:

• Product-managing the various possible portfolio pieces
• Considering overall positioning and messages that reflect that positioning
• Selecting and preparing to measure the appropriate primary actions that denote success for the site

It’s probably sensible to go after the hardest part first: the portfolio pieces. Watch this space.

I’m not a fan of LessWrong – while I like the idea of being more rational, and strive to acknowledge and feel my emotions but not let them impede my thinking needlessly, there’s a strong whiff of holier-than-thou coming off of many in the rationalist community, including the otherwise very interesting Scott Alexander, whose writings on mental health care I admire. A little humility goes a long way but it is sometimes in short supply.

Nonetheless I was happy to read Anna Salamon’s article Humans are not automatically strategic. Though the article makes heavy use of the trope of calling the less-rational populace “humans,” as if rationalists are somehow better than mere humans, the core of the piece lays out an eight step process to develop and pursue goals that is very much like the method I came to the hard way over many years, and try to coach the people I support into using.

(a) Ask ourselves what we’re trying to achieve;
(b) Ask ourselves how we could tell if we achieved it (“what does it look like to be a good comedian?”) and how we can track progress;
(c) Find ourselves strongly, intrinsically curious about information that would help us achieve our goal;
(d) Gather that information (e.g., by asking as how folks commonly achieve our goal, or similar goals, or by tallying which strategies have and haven’t worked for us in the past);
(e) Systematically test many different conjectures for how to achieve the goals, including methods that aren’t habitual for us, while tracking which ones do and don’t work;
(f) Focus most of the energy that *isn’t* going into systematic exploration, on the methods that work best;
(g) Make sure that our “goal” is really our goal, that we coherently want it and are not constrained by fears or by uncertainty as to whether it is worth the effort, and that we have thought through any questions and decisions in advance so they won’t continually sap our energies;
(h) Use environmental cues and social contexts to bolster our motivation, so we can keep working effectively in the face of intermittent frustrations, or temptations based in hyperbolic discounting

Point (a) seems to be where so many people fail. What is it that you want? What should happen? If it were magic, where would we be already? Some of this is using question (b) to back into (a), which can be easier, sometimes. But (b) is really about measurement—making your goal operational.

(C) and (d) are research. People often forget to do this, or find it unexciting. That could be a clue that you’re not as interested in your goal as you thought (see point (g)), but in these times many find our intellectual persistence has been weakened by the many available distractions of social media, especially the FOMO that comes with that. It’s all to easy to envy or look down on anyone you come across on Twitter, Instagram, etc. and it doesn’t help you be you if you are buys inspecting others.

(E), systematically test many different conjectures, is an advanced form of what I wish people. would do, which is just try something and see how it goes. That makes a lightweight form of (f) possible—see if what you are trying is working, and make a change if not, based on (b). (H) is similarly advanced. A lighter form of this, more than adequate to start, is to take notes on your plan and results so you can refer to them later, and do so.

Any creative professional (and I use the term broadly) eventually needs to create a system for themselves (or adopt and then adapt one) to organize their thoughts and plans. One’s head is the least reliable storage. Doing so can help make being strategic possible.

To me, someone who didn’t go to business school, the all-too-common admonition to “make the business case” for something was often a showstopper. What is a business case, what does it include, how do I make one, and what hard questions need be answered when making it? I had no idea where to start. And even my best bosses were no real help, handwaving vaguely about time and costs and benefits and whatnot.

It turns out that, aside from some large businesses that have a very specific format for an internal proposal, they were handwaving vaguely because they didn’t have anything more specific to say, and because some of their words carried meaning that wasn’t obvious.

It took me a long time to figure this out. I finally pinned someone down while I was early at Belkin and fairly interrogated them about the “business case” that seemed so daunting throughout my career, and learned that there’s not really much to it. You could bash together a business case for whatever without too much trouble, I bet.

Sure, there’s the matter of benefit—that’s a bit of business jargon that refers to the desirable result of doing a thing, said in a way that doesn’t depend on how it is achieved. For example, we would like to have a more inclusive workplace. There are lots of things we could do to get there. Improving the inclusion of underrepresented groups in our hiring pipeline is one tactic we might use to help achieve that benefit.

So this business about benefit, time, cost, etc. is correct, and really about expressing a problem, a benefit to counter the problem, and then offering possible methods and their costs that will help achieve the benefit.

I wrote a little memory jogger to help build these. It’s not much to look at; I’ll bet you can fill it out pretty easily as you think about a problem you are trying to solve. A simple proposal, not too expensive or time consuming, can be just this in an email. A fancy proposal will need more flesh, but the anatomy is the same:

We have (problem)
It costs us this (in treasure, pain, missed opportunities)

A way forward is (solution)
It will cost us (how much) to get started (in treasure, people, space, equipment, etc.)
In the first (timeframe) it will yield (result), based on (the similar experience of others)
Ideal for us is if it ramps to producing (result)
Other opportunities it might create include (stretch)

There’s also (alternative solution)
It’s better than the other (because)
It’s worse than the other (because)
It will cost us (how much) to get started (in treasure, people, space, equipment, etc.)
In the first (timeframe) it will yield (result), based on (the similar experience of others)
Ideal for us is if it ramps to producing (result)
Other opportunities it might create include (stretch)
Etc.

Any part of this you can’t answer can be answered with the help of folks in your organization, folks you know or learn about via working the network, or can be left asked but unanswered. You’ll need to talk to these people anyhow to gather support for your proposal, so you might as well include them early—involving people in creating the future that they will be part of is really the only good way to create buy-in.

Recently I’ve started to knock this sort of thing together into a little proposal format. It doesn’t match the above exactly, but you’ll recognize the themes.

A specific and action-oriented name for the initiative

Background

Explain the situation that gives rise to the problem and any useful facts about the situation that will be good to know as people read through the proposal.

Problem

Express the specific problem you’d like to go after, more plainly and directly than suggested in Background.

Our Aim

State the desired benefit. For example,
Elevate the average employee’s awareness of inclusive work culture and behavior, and equip them to participate in small local interventions when necessary.

Proposed Intervention

Explain the concrete steps you plan to take to achieve the benefit.

Cost and timeframe

Talk about what it would cost, and how long it would take, to do those steps. Consider initial costs, recurring costs, whether we’re “done” at some point. Bonus points if the costs and time line up exactly with the activities in the proposed intervention.

That should be enough to get most ideas out of your head and into active discussion in your company, club, homeowners association, etc.