Stolen Stuff for You to Steal

For a long time, I assumed that I was the youngest person in any conversation. That was often true and uncomfortable. Over the past few years, I’ve frequently had the even more uncomfortable realization that I am now often one of the oldest. Nicely, along that journey I’ve had the opportunity to work with a lot of really smart people and steal stuff from them. Below is the most valuable stuff I’ve stolen — the learnings that shape my thinking every day. If you find any of this to be valuable for you, please steal it from me. If you are also a thief, I’d love to learn about what you’ve stolen and find valuable.

The Fundamentals:

Most of the good things I’ve stolen fit nicely into 3 buckets:

Fixated on Problems / Flexible on Solutions

I think people are really good at identifying the existence of problems — when I say problems, I mean things that should be better in the world / could be improved upon if someone did an excellent job implementing a different approach.

In contrast, at least in my experience, it turns out that solutions are much more elusive — when I say solutions, I don’t mean potential solutions, I mean something which when put into practice actually sufficiently improves upon the way that a particular problem is addressed such that people chose to stop doing the thing they were doing before and start doing your new thing instead.

As such, it is helpful for me to ground myself in:

  • It is important to align on a clear, specific definition of the problem I am attempting to solve (solutions are hard enough when the problem is clear)
  • I am probably wrong in some important aspect of my current potential solution
  • Therefore it is helpful to think of everything as a prototype…and start simple
  • Which, if I am doing it right, will help me learn quickly and iterate
  • The data and insights from engagement with my prototype is the best way I have to rapidly learn, so I need to design specifically for data and insight gathering

(note: I think the above applies equally to problems big and small, fundamental and tactical)

Resource Allocation

Our ability to solve problems is a function of how we choose to allocate our resources toward solving them — therefore, I’ve found that one of the most important aspects of my work is collaborating with my colleagues to determine how we should allocate our scarce resources across problems. I think it is helpful to remember that in retrospect your resources were always allocated… you can either do so intentionally or outsource those decisions to the whims of the universe. If 2020 has taught us anything, I think it is now clear that the whims of the universe are not always kind. Resource allocation (planning/priority setting) processes can feel painful, but they are much, much better than the alternative.

Company Building is a Human Endeavor

The most important, expensive, and confounding resource I’ve been responsible for allocating is my time and that of my human colleagues… companies are human systems… humans are complicated.

Like I think many people, I’ve traversed a few important phases in my career:

  • Phase 1: Can I please be a people manager / build / grow my team?
  • Phase 2: People are hard; can I please go back to working on interesting problems?
  • Phase 3: Collaborating with exceptional colleagues is the best part of work and the opportunity to lead people is the most rewarding and valuable element of my ongoing personal self-improvement journey.

I’ve been significantly more effective in Phase 3 than I was in Phase 2 (and felt better and enjoyed my work more).

More than anything, what I’ve learned is that my colleagues are much like me. They have self-doubts, anxieties and ambitions. They want to learn and get better without too much embarrassment along the way. They want to feel like their work is important and meaningful and understand how it fits in with the work their colleagues are doing. They want their colleagues to like and care about them.

Simple enough in concept. The hardest of hard things in practice.

The Tools:

Ok, if you are still with me, here are some specific tools which seem to me to make each of the Fundamentals described above easier / better:

Fixated on Problems / Flexible on Solutions

SCQA: To specifically define and align on the problem you are attempting to solve and how you intend to go about doing so, I have found Barbara Minto’s Pyramid Principle to be an invaluable resource. Specifically, her Situation, Complication, Question, Answer (“SCQA”) framework. Tactical tip: I find that it is very helpful to have one and only one “Question” per instance of this framework… if you are tempted to have more than one question, you are likely working on more than one problem and you should create one instance of this framework for each.

Make an Equation: Once we have aligned on a well-defined problem, I find it helpful to express the solution space in the form of a simple multiplication equation, with the thing to the right of the equal sign being the thing I want to make better and the factors on the left of the equal sign being the levers available to me to do so. For example, if the problem I am attempting to solve (as expressed in the “Question” which you identify by using Minto’s SCQA framework) is, “How might we generate more revenue from our website?”, you might create an equation which looks something like this:

Visitors x Conversion Rate x Order Value = Revenue

While seemingly simple, I find that taking the time to write this out explicitly is game changing in my ability to rapidly iterate toward an impactful solution.

Why?

  • The equation makes it really clear what my options are for working on my problem. In the above example, I can try to increase visitors, improve the conversion rate, or increase the order value… that’s it.
  • I know a lot more about what data / insights I need to gather to guide my iterative work toward a solution. In the above example, I need frequent, reliable access to data on visitors, conversion rate, and order value.
  • My colleagues and I now have a clear shared language to use to discuss the hypothesis we are testing. For example, I hypothesize that our best path to increasing revenue is to improve our conversion rate — in order to do so we are going to try ___, ____, and ____.
  • When picking a factor in the equation to optimize, I can also easily identify the other factors I need to watch to see the secondary impact my potential solution creates. I refer to the other factors I am watching as “quality” measures. For example, using the equation above, if we are optimizing for growth in Visitors, I want to keep an eye on Conversion Rate as a quality measure on the new Visitors I am attracting.

Guessing: I find it very valuable to write down a guess of how I think a thing I am about to try is going to play out — it’s best if I can do this in terms of one of the factors in my equation I described above.

  • Prompts me to think through what I am trying to accomplish with the thing I am about to try and if it realistically could have the impact I desire.
  • Enables honest reflection on how the thing went vs. what I expected and consideration of why it might have done better or worse.
  • It’s fun. Get your team to do it, have a contest.

Note: I use the word “guess” very intentionally here — more formal activities like “forecasts” certainly have their place, but I find that a quick guess is a very low-effort, high-impact activity.

Experiment Design: While it is wonderful when we try something and it works fantastically, in my experience that is more rare than frequent. Given this, I’ve found it helpful to keep front of mind that discovering quickly that I was wrong is the second best result when I try something and “meh” is the worst. I think the best way to avoid the complexity of “meh” results is to put some thought into intentionally designing your experiment such that it is most likely to yield either a clear yes or a clear no… and then if you get a “no,” be proud of yourself; your experiment design just saved you a bunch of time and made you smarter.

Shorten Baking Periods: One element of experiment design which I think merits a special call out is the value of designing tests (and analysis more broadly) such that you can get results quickly. The sooner you have results from one experiment, the quicker you can digest the learnings and move on to your next experiment. The more distinct experiments you can fit into a time period, the more you will learn.

As one example, I find it helpful to use metrics such as conversion (or repeat purchase, or lifetime spend) as of X days of user lifetime (where X is a small number like 1, 7, or 14 days). This enables you to compare user cohorts with like-to-like data much more quickly and avoids conversations when comparing cohorts which inevitably have to include the caveat, “…but the more recent cohort is still baking”.

Keeping It Simple: A former colleague coined (or stole and used frequently) what quickly became one of my favorite phrases: “Tell me a story that starts with your idea and ends with us making money and keep it as short as possible.” Such beauty in that simple, memorable turn of phrase… With all due respect to Rube Goldberg, I strongly prefer potential solutions which offer an uncomplicated path to impact.

Start with a Passionate Niche: Most of my favorite products first offered a limited feature set which appealed deeply to a niche of users or use cases. Success in delivering something loved by this small group enabled the product to mature over time into its now more fully formed self.

One of my favorite examples of this is Google Sheets. Excel is an amazing product which has created a staggering amount of value in the world — at the time Google Sheets was created, Excel seemed invincible. Cleverly, Google Sheets focused on one thing which Excel did very poorly — collaboration. In focusing on collaboration, the initial Google Sheets product neglected obviously critical features for spreadsheet users, pivot tables being but one example. Despite the lack of obviously required spreadsheeting functionality, Google Sheets appealed deeply to users and use cases for which collaboration was important. Now, many years later, Google Sheets has pivot tables.

Strategically Unique Customer Acquisition: It is often really hard for a new product to cost-effectively acquire early customers via channels like Google and Facebook which are pretty efficient advertising marketplaces. In an efficient advertising marketplace, the products/advertisers that will acquire customers cost-effectively will be those with the most tuned conversion funnels — new products do not yet have tuned conversion funnels. As a result, to get the critical insights and learning which come from real people using your product, I’ve found that it is often helpful to craft a strategically unique approach to customer acquisition bespoke to my new product.

When crafting a strategically unique customer acquisition strategy, I like to ask myself two key questions:

  1. What do I know about the characteristics of the potential passionate customers in my targeted niche? Which of these characteristics distinguish the folks who will be passionate about my product from other people who will be less passionate? The more specific I can get the better… demographics are nice, but specific behavioral characteristics are way better, because they set you up to answer question 2…
  2. Where/how do people who have the identified characteristics of these most passionate potential customers self aggregate (hang out together) already (even in relatively small numbers)? Bonus points if I can identify places where the folks I am looking for self aggregate at the exclusion of folks who do not have the characteristics I am looking for.

By way of example, at Craftsy when we discovered that our initial target niche was people with an existing deep passion for quilting, we found magazines / communities / newsletters like this one: https://www.quiltingdaily.com/ … our most likely passionate customers were subscribers… and if you did not have an existing deep passion for quilting, chances were super low you would spend any time there. This meant that we could acquire customers quite cost effectively through that channel with little/no competition… at least until we ran the pool dry.

Obviously, the magic is in figuring out what those distinguishing characteristics might be for the folks who will have the most passion for your product.

Note: I find it helpful to keep in mind that the scalability of a customer acquisition channel or strategy may be inversely correlated with my ability to execute against it successfully for my new product. Highly scalable strategies have likely already attracted products that are prepared to scale and thus these strategies will be competitive and expensive. With a new product, relatively small pools of potential customers can be incredibly valuable as they enable you to learn critical lessons, and are often overlooked by more mature products.

Resource Allocation

Better than last time, worse than next time: Resource allocation / planning processes are sometimes not the most fun. I’ve found that simply saying aloud (and meaning it) that your goal is that your current planning process is “better than last time, worse than next time” can be like casting a magic spell. Resource allocation processes are prototypes too and it is helpful to remind yourself and your colleagues of that reality and give yourselves some grace accordingly.

Frameworks — the magic is in adoption: Thanks to decades of management consulting and the resulting millions of slides, the world is overflowing with frameworks. Frameworks are basically a way for us to bring structured thinking to complex problems… and relative to the chaos of approaching a complex problem without a framework, most frameworks are wonderful. However, it is easy to get overwhelmed by the volume of frameworks available to us — this often results in many frameworks getting introduced in a company without any getting used consistently. I can’t tell you the number of times I’ve attended an expensive company sponsored training on something taught by a terrific expert who introduced a great framework that was then never used by anyone in the company after that session.

I find it valuable to, in collaboration with my colleagues, pick a few frameworks which we will use on our team / in our company and strive for heavy adoption… to the point where the chosen frameworks become something of an inside joke. When people were using SCQA at Craftsy to decide where to go to lunch, I felt like we were doing something right.

Separate apples and oranges: One of the most complicated aspects of resource allocation is that it is often all about choosing how to allocate resources between dissimilar types of objects. When this is the case, I find it helpful to first group dissimilar objects into buckets of similarity, allocate resources across the buckets, and then allocate resources within each bucket to the objects you sorted into that bucket. Below are 3 different examples I like of ways apples and oranges separation can play out in practice:

A. Horizon 1 / Horizon 2: “Horizon 1” refers to activities which are expected to deliver meaningful in-period benefit… in contrast, “Horizon 2” describes seeds you might choose to plant today which will not deliver value until a future period. I like this approach to apples and oranges separation for its simplicity — I also think it illuminates nicely why apples and oranges separation is helpful in your resource allocation efforts.

Using our example equation from above is helpful here — if you are trying to increase revenue, you might have the opportunity to allocate resources to a) testing small changes in your conversion funnel and/or to b) developing and distributing content to drive organic growth in visitors. While both are potentially compelling, they are really difficult to trade off between because the time horizon for impact is very different between the two. Often, when this is the case, I’ve found it (too) tempting to opt for the initiative focused on near-term impact. Pulling up and first deciding that it is important to allocate some resources to Horizon 2 initiatives makes it easier for specific initiatives to compete like vs. like and helps prevent urgency from crowding out important longer-term investment. My future self thanks me when I do this.

B. Prototyping vs. Scaling: I also find it really helpful to separate activities by their relative maturity. If I am working on a new problem or a new solution space, I am “prototyping.” If I have found something that works (likely as a result of an intentional prototyping effort) and I am now trying to increase its impact or optimize it, I am “scaling.”

Clearly distinguishing between the two is helpful because they should have different kinds of goals, different processes / approaches to the work, and more often than not different resources… In my experience, each of us are usually either better at prototyping or better at scaling and asking someone who excels at one to do the other often does not go as well as I hope it will.

C. 3 Product Buckets: My former colleague, Adam Nash, codified what I think is a great example of apples and oranges separation applied to product prioritization. He advocates (better than I could here) for classifying potential product features into 3 buckets: Metric Movers, Customer Requests, and Customer Delight.

Allocate 10 points: When collaborating with my colleagues on resource allocation, once we’ve aligned on a framework for separating apples from oranges, it is then helpful to ask everyone to (privately) allocate 10 points across the different buckets (representing how each person would choose to allocate resources on a relative basis between the buckets) and then share and discuss.

Much like “guessing,” this approach is best done quickly and most of the value in it comes from the discussion that follows. This activity helps everyone involved feel the resource scarcity, struggle with the tradeoffs, and naturally prompts questions between colleagues like, “I only allocated 2 points to ____; what drove you to give it 6 points?” which will lead to really valuable and often illuminating conversations.

Pick dials to enduringly turn up to 11: I will caveat this by saying I have no idea if this is actually true, in fact I made it up: I imagine that 20 years ago or so, some group of leaders at Amazon got together and concluded that two things mattered most to eCommerce consumers and whoever won on these two dimensions would win: 1) Fulfillment Speed; 2) Product Selection. In my story, ever since that initial moment of recognition, they have focused maniacally on turning the dial to 11 on both of those dimensions… Prime / Two Day Delivery / One Day Delivery / One Hour Delivery… DRONES! Amazon may have received early accolades for their ratings and reviews or product recommendations…but how much have they really done over the past 20 years to improve on those experiences… or the user experience of their website more broadly? Seemingly (at least comparatively) not much at all… but how much have they expanded the product selection they offer? Well, mostly books → mostly everything.

I think it is massively helpful to strive for similar insight and focus in my products and companies.

  • What are the 1, 2, or maybe at most 3 elements of my product experience that should matter most to my customers over time?
  • How can we, through maniacal focus, consistently strive to crank it up to 11 on these elements?

Company Building is a Human Endeavor

Allocate time for meeting people: In the resource allocation I do of my own personal time, I find it helpful to carve out a specific window on my calendar dedicated to first conversations with people I have not previously met. I’m an introvert, I don’t naturally gravitate toward meeting new people… in fact doing so makes me uncomfortable. However, I recognize that my personal and professional network is my most valuable asset and investing in building relationships is always worth the time allocation and potential emotional discomfort. To hold my focus on investing here, I reserve 30–60 minutes on my calendar each week for first conversations… and let the calendar hold taunt me until I fill it.

Sometimes I leave these conversations questioning if I would have better spent the time on some urgent item of the day… but inevitably a few days, or weeks, or even months later that first conversation from back when unlocks something important for me. I find this to be particularly helpful in recruiting — it is wonderful when I need to hire for a new role and recall that I met someone some time ago who would be perfect for it or knows someone else who would.

Focus on Strengths: I still remember distinctly when one of my favorite managers at eBay explained her point of view that we would succeed as a team by each focusing on our strengths, rather than working to individually overcome our weaknesses. My mind was blown. Up until that point in my career (and life), I had spent a ton of energy on painfully trying to chip away at my many shortcomings. Since then, I have become an increasingly deep believer in this philosophy — our unique strengths are what enable us to have differential impact and the magic is in finding things to work on which play to those strengths… while recognizing our weaknesses and ensuring that we structure our work and our teams in ways that offset those weaknesses. That said, if your weakness is that you are kind of an asshole, you should please stop being an asshole. :)

Amplifiers and Complements: Consistent with the above suggestion to focus on strengths, I am an enthusiastic believer in the benefits of a diverse team, on all dimensions of diversity — diversity is what enables us to focus on our own strengths while ensuring that as a team we excel in all of the ways we need to excel. That said, I’ve found that when building a team, I am more effective if my very first hire / co-conspirator is more of an amplifier than a complement. By amplifier, I mean someone who helps me make the most of one of my core strengths, typically because they too are strong in that area and as such are able to push my thinking and prompt me to strive to elevate my own game. As the team expands from 2 to N, I then focus on hiring complements to offset my plethora of weaknesses… while striving to ensure that each of those folks also have an amplifying colleague who helps them maximize their strengths.

One Question: When hiring senior leader colleagues, I have found one interview question to be far more valuable than all the others I tend to ask:

“Who specifically will want to quit their job to come work with you when they find out that you are joining us?”

Any outstanding leader with significant leadership experience should have at least a few former colleagues who would jump at the chance to work with them again. Those former colleagues know way more about the person I am interviewing than I will ever be able to discern from my other questions and the quality of those colleagues and their enthusiasm for my candidate will speak volumes.

Avoiding Organ Rejection: Onboarding as a new leader into a high growth company is really hard and often goes poorly. This is particularly true if many/most of the company leaders have either been in leadership roles for a long time / since founding or have rapidly been promoted into leadership roles based on all that they have accomplished — in companies like this, the currency of credibility is earned not bestowed and as such the new hire starts with zero chips. I’ve found that a couple of relatively simple, but non-intuitive things make a world of difference in enabling high quality leaders to onboard successfully:

  1. Narrow the initial role: Leaders often ask for an expanded role when considering taking a job at a new company and in many cases are very capable of taking on the challenge this brings. However, I’ve found it very beneficial to help them recognize that as compared to their current job, they are going to have a big learning curve ahead of them — companies and teams are always more complicated than they appear from afar… and as such they would be well served starting with a more narrow scope which plays directly to their greatest strength, with a shared commitment to rapidly expand scope as the new leader progresses down the learning curve and builds credibility. This approach helps the leader approach their new role with confidence and add compelling value for their new team, which is a great platform from which to build.
  2. Avoid the temptation to impress up, instead lift up peers and directs: It is human nature to want to impress your new boss… but as a new leader, your new boss is likely the last person you need to impress. Your new boss just hired you, is a believer in you, and is highly invested in your success. In contrast, it is not uncommon for at least some of your new peers and direct reports to have doubts, concerns, or competitive thoughts (why them and not me). While your new boss is thinking of the leverage and experience you will bring to the team and the ways you will make her more effective at her job, your new peers and directs may feel like you have made their aspirations for advancement more complicated. These folks often did not make the decision to hire you, may not have been directly involved in the hiring process, and even if they were, they likely spent far less time with you than your new boss. So, I’ve found that it is critically important for new leaders to focus for the first few months on lifting up the work of their peers and directs — helping each of them as individuals and as a team accomplish their goals more easily and/or effectively.

Ownership: I think this is the most important section of this whole thing… and took me the longest to really learn — honestly, I am still learning it. I read the Netflix Culture Deck too many times to count and it resonated deeply with me — it put articulate words to my desires as a junior-to-mid-level employee. Nonetheless, as a leader, when I felt like something was important, when I felt pressure (self imposed or otherwise), I gripped the wheel ever-tighter — leading with more control and less context, keeping ultimate ownership safely secured in my possession. I told myself that I was doing this for the benefit of not just my company, but also my team — they didn’t want to have to carry the burden of taking bold positions which would often prove to be wrong, they would benefit from my years of experience — no need for them to make mistakes I had already made, etc…

That was some bullshit and was a disservice to my company and my team.

I have grown to believe that enabling clear, focused problem ownership with complete context throughout my team is the most impactful thing I can do as a leader.

  • Owning problems is a required unlock for driven, talented people — if they don’t get this opportunity working with you, they will eventually leave for the opportunity to do so elsewhere. While they still work with you, they will only deliver a fraction of the value they could create if they had clear ownership of focused problems and complete context. Ownership attracts, retains and unlocks talent.
  • If at the end of the day you own everything, the solution space you are exploring is limited to what is in your head… and the implementation will therefore always be as imperfect as your ability to communicate what is in your head. Ownership increases the breadth and quality of your potential solution space exponentially.

Given the importance of ownership and my natural tendency to hoard it under stress, I have found a few tactical things particularly helpful:

  1. Where possible, organize teams around problems. Functional leadership is valuable for honing the craft of each functional discipline, recruiting and evaluating talent, and peer-to-peer learning and camaraderie — so I am not suggesting abandoning traditional org structures is necessarily the right thing to do. However, what I have found is that magic happens when you can form a team of the people needed to truly own a problem and work together toward a solution — in some cases this could become the formal reporting structure in your organization, or it could be done via “squads” while formal reporting remains functional. What is important is that each team has a very clear mandate — a problem that they are responsible for working to solve. I find that organizing teams around problems also makes your resource allocation decisions tangible in a helpful way — you can clearly see what % of resources have been allocated to each problem on which you’ve chosen to focus.
  2. Strive to be inquisitive or a teacher. When I am doing this well, I successfully resist the temptation to tell my teammates what I would specifically do to solve a problem they own — instead I get curious and ask them questions about how they are thinking through the problem, and, where helpful, teach them a framework or structure I might use to think about the potential solution space.
  3. Help your team move from asking for permission to communicating intention. If you have to ask for permission to do something, do you really own that thing? Nope. For me, this is a helpful check on if I’ve enabled real ownership. However, distribution of ownership does not mean that keeping your colleagues informed about what you are doing is no longer critical — as such, I think it is helpful to intentionally replace asking for permission with communicating intention — this provides your colleagues an opportunity to share helpful feedback before something is underway, but keeps ownership of the problem with the intended owner.

Hold focus on: In my professional vocabulary, I have found it helpful to replace the word “accountability” (which is often used with a negative connotation) with the phrase “hold focus on.” To me, when people discuss professional accountability, they typically are combining three distinct things:

  1. Did you work on the right stuff?
  2. Did you work smart and hard on that stuff?
  3. Did you deliver the expected results?

As discussed at length above, it is clearly my responsibility as a leader to help my colleagues work on the right stuff — this starts with resource allocation, but for resource allocation to translate into the intended actions, as a leader I need to ensure that as a team we hold sustained focus consistent with that allocation.

I never want it to be my job to make you work appropriately smart / hard. If I find myself having to do that, I really messed up hiring. Driven, talented people push themselves and hold themselves to a high standard of effort — those are the only people with whom I want to work. If I find myself working with someone who doesn’t fit this profile, I shouldn’t provide more “accountability,” I should help them find a different place to work.

Delivering on expected results is a function of the two things above which we can control — holding focus and working smart/hard… as well as many, many things which we can’t always control.

As such, I find it helpful to communicate that rather than having a culture of accountability, I will as a leader ensure that we “hold focus on” our agreed upon priorities… each of us as great colleagues should take personal responsibility for working smart/hard… and that if we do this, we have maximized the probability that we will achieve our desired results.

How are you?: I begin 1-on-1s with my colleagues by asking, “How are you?” … after they answer, typically with some socially appropriate bs generalities, I then follow up with either: “really though, how are you?” or “said with some hesitation…” — just this little additional push tends to break us out of the realm of bs, and helps us get into a substantive conversation.

This is not our last job: I always want to work in a culture where colleagues are advocates for and supporters of each other — especially across any elements of workplace hierarchy. I have found that cultural objective is consistently undermined when it is taboo / inappropriate / disloyal to consider job opportunities outside of your current company. Simply put, as your manager, I am not really your advocate or supporter if my support only exists within the confines of our current shared workplace. To address this I try to find frequent opportunities to publicly discuss the fact that this is, at least for most of us, not our last job… and that is not a secret… so no need exists for any of us to pretend like it is. If someone wants to leave my team or company, I want to be trusted by them to help them do so — and when I am, this is a clear signal that we are building the culture we want.

Quick Transitions: When someone on my team is leaving, regardless of reason, experience consistently suggests that collaborating with them to set a transition timeline which is as short as possible is genuinely best for everyone. By short, I mean very short — once it is decided that someone is leaving, rarely do I find it valuable for them to continue to work on my team for more than a couple of days. Announce the departure, celebrate the team member’s past contributions, be genuinely excited for what lies ahead for them, ensure that handoffs are clear and specific and that work-in-progress is well documented… then help everyone move on… which includes helping the person departing transition successfully and smoothly into the next phase of their career.

Bonus Plans: I have learned to hate them and wish they didn’t exist. This is particularly true for two reasons:

  1. Goals change — if a new product or company is doing a good job of learning quickly, it likely benefits from the flexibility to adjust goals based on these learnings… in contrast, bonuses often necessitate locking in goals for some period of time and thus can get in the way of building a nimble, learning-focused team. To mitigate this, you can set goals which are far less likely to change — like company Revenue or EBITDA — however, I would argue that a) if what you are trying to incentivize is some kind of extra individual effort, I am skeptical that a goal which is in many ways outside of the direct span of control of the individual is effective in this regard, and b) equity / option plans are a far better way to align incentives in this regard as they are comparatively less prone to tempt short-term optimization and tangibly support an ownership culture
  2. Expectation setting — Many people have worked in larger company environments where bonuses are paid at / near / or above target almost all of the time. This results in an expectation that if a bonus plan exists, they can count on receiving the target payout. When that is the case, either the bonus is now a more confusing version of base compensation (rather than have a bonus plan, just increase base comp) or it creates major disappointment and frustration if the bonus does not end up paying out at 100% or more of target.

Walking Around: I try to find at least a few times per week when I can wander around the office, find someone who I have not engaged with 1:1 for a little while who looks interruptible, and try to prompt a spontaneous conversation about something interesting they are working on. Not only do these walk-arounds create nice opportunities for relationship building, a disproportionate number of compelling new ideas or alternative approaches to problems seem to naturally emerge from these conversations — I think as a result of their informality and free flowing nature. I especially like to try to do this if a meeting I had scheduled cancels or something else prompts some unexpected unscheduled time.

In an increasingly work from home / distributed team environment, I think it is important to find substitutes for this in-office routine.

3 Things, 24 Point Font, Repeated Constantly: All of the hard work we’ve done to ensure that we have prioritized and organized around the right work is only as good as the team’s ability to hold these priorities clearly in their heads so that they can use them to make decisions consistent with those priorities / objectives (if I come to a fork in the road, which way should I go?). Ensuring this happens is a core leadership responsibility and is a whole lot easier if we:

  • Keep the # of objectives as low as possible — 3 is great, 4 is maybe ok
  • Make them simple and memorable — ensuring that each objective fits nicely on one line on a slide using 24 point font (or larger) tends to to be a good check for me to make sure they are simple enough
  • Repeat them again and again… and again and again. Then do so again. Every chance you have / in every venue — company meetings, but also team meetings, 1:1s, casual conversations, new hire orientation, etc…

We believe _____ therefore ____: I frequently encounter use cases where I find it helpful to draft a story for internal team consumption using the following simple five part format:

Part 1: We believe(d) _______

Part 2: Therefore we _____

Part 3: As a result we learned _____ and therefore we did _____

Part 4: This enabled us to achieve ________ customer and business impact

Part 5: Based on this, next we plan to ________

I also find it helpful to write a draft version of this story when I start working on a new problem, pretending that I am my future self looking back — this is basically a narrative and more thorough form of guessing.

Narrative Vision Doc: As part of the effort to clearly and repeatedly share company and/or team priorities, I find it helpful to create and share widely a narrative doc written in the speaking voice of a leader on the team (casual language, avoiding business jargon) which walks through the progression from medium-term vision (~3 years out) to current priorities. I like using parts 1 & 2 of the story format described above to build the bridge between the vision and priorities: “we believe ____ therefore _____”. I know that I’ve hit the mark with this doc when managers share it unprompted with new hires as part of their onboarding.

Separate Meeting Pre-Read and Discussion Guide: A simple approach which I have found to be game changing for structuring board meetings has proven to also be valuable for making meaty team meetings productive — create two separate packets of materials to structure the conversation:

  1. a pre-read
  2. a discussion guide

I don’t think format matters much — these can be decks, docs, spreadsheets, etc… or any combination. What matters is that:

  • The pre-read and discussion guide are clearly distinct from each other
  • The expectation is that everyone reads, processes and prepares questions based on the pre-read ahead of time (in some cases it may make sense to carve out some time at the beginning of the scheduled meeting for everyone to consume the pre-read if they have not had time to do so)
  • No time is spent in the meeting walking through the pre-read. You can dedicate time to discussing the questions prompted by the pre-read, but do not walk through the pre-read… this defeats the purpose
  • Meeting time is dedicated to the agenda outlined by the discussion guide

This helps ensure that meeting time is used primarily for productive discussion / building on each other’s thoughts and ideas, rather than one-way dissemination of information.

If the meeting is recurring (like a Board Meeting, QBR, etc…), it can be really helpful to create a standardized template for the content of the pre-read and then simply update it with the data and insights from the latest period — not only does this save a bunch of time in preparing the materials (and divvying up work), it also makes consuming the pre-read much easier for your attendees as they do not have to orient themselves to the way the information is shared.

Rotate Meeting Ownership: I realized recently that when I lead a meeting, I naturally structure it / design the meeting in a way which aligns with my style and needs. As it turns out, if I have successfully built a diverse team, other folks on my team may not find my meeting design to be the one which enables them to be their best selves. As a simple solution, I’ve found it helpful to rotate meeting ownership for recurring meetings, ensuring that the owner of the meeting has full flexibility to design the meeting however they want. When this works, it has the potential to prompt greater diversity of participation and engagement.

Ask Me Anything: One of my favorite ways to support a culture of transparent communication is to periodically schedule a meeting where I (and/or other leaders) will answer any and all questions, unscripted. I find it most helpful to ask people to submit questions ahead of the meeting so that we have a rich pool of questions to answer. I then put the questions up on a screen, read them aloud and answer each and every one of them in order until we run out of time. If some of the questions are silly, some are insightful, and some are uncomfortable, I feel like I am doing this right and have the opportunity to live the culture of transparent communication in which I strongly prefer to work.

Small Group Lunches: In addition to the full-team “Ask Me Anything” described above, I also find it valuable to host regular small group lunches where the agenda is a very informal opportunity for anyone to ask me questions and/or to raise things that are causing them frustration. Especially when managing a bigger team, I find these to be an important vehicle for: a) keeping a pulse on what is confusing or concerning for folks on the team, and b) ensuring that everyone on the team feels like they have a direct relationship with me / know me personally and can therefore ping me anytime I could be helpful for them.

As a bonus, I find these lunches to be great venues for trying out ways of discussing important topics which I plan to subsequently bring to an all-hands or bigger team meeting — the smaller group size lets me get a better read for individual reactions and uncover inarticulateness on my part in a forum where it is easier to take another stab at discussing something if I miss on my first attempt.

Ok, you made it to the end… that’s all I’ve got. If you have interest in discussing anything you’ve read here, please reach out.

NOW: @ home, a lot. dad. some boards. THEN: President @ Guild Education, co-founder @ Craftsy (NBC), HomeAdvisor, eBay, Bain & Co, Berkeley, Michigan, Detroit.

NOW: @ home, a lot. dad. some boards. THEN: President @ Guild Education, co-founder @ Craftsy (NBC), HomeAdvisor, eBay, Bain & Co, Berkeley, Michigan, Detroit.