TBM 18/52: Product Manager to People Manager (and My Big Mistake)

After a 15 year hiatus, I recently made the shift from product manager to people manager. I made a big mistake that impacted people I care about. I’ll share it here for other IC product managers turned people managers.

The mistake? I didn’t ask the individuals on the team “What does clarity really look and feel like?” early and often. And then meet those needs and resolve differences.

The reality is that people crave different types of clarity. There are overlaps, of course, but there are differences. Sometimes the differences are very subtle. If you don’t really listen, you might assume people have the same needs (especially if they use the same words). Or you might assume they have different needs because they use different words.

Words like role clarity, strategy, plan, purpose, career plan, and direction are slippery. Ask five people to define strategy, and you’ll get five, very different answers. Ask what having “a plan” feels like, and you might get more useful answers:

  • I know exactly what I’ll be working on for the next couple weeks

  • A clear idea of Who we are trying to serve

  • A rough idea of the impact we’re trying to create…”plans will change, of course”

  • A sense of our big risks, and how we’ll try to address those

  • How what we’re working on will impact my career progression

OK! We’re done! No. You’re just getting started. Take each of those statements and dig further. “Can you tell me more about that? What does it look and feel like?”

  • A list of tasks and to-dos with clear roles and responsibilities

  • A persona that looks like this [shows persona]

  • A metric. I need a North Star Metric like this [describes metric]

  • I need to know there’s a risk of not failing in the eyes of the executive team

  • Point by point, how the next year’s projects will set me up for [Role X]

We’re three levels deep, and not done yet! There are more conversations to be had. Those conversations will end with core human needs around safety, acceptance, and purpose. You have to go there. 

On a cross-functional team people always have conflicting needs. One person’s need for clarity involving X (and that looks like this) is in direct opposition to another person’s need for clarity involving Y (that looks like that). Meeting one person’s needs may completely invalidate another person’s needs. Function X tends to approach things differently than Function Y. The team may be able to work it out in the open. But that can be very difficult. 

This is your first priority, otherwise things will be much harder to fix later.

Product managers (my background) toil in white space all the time. The work is hard, and takes continuous tweaking to get right (until it goes wrong, again). But product managers aren’t people managers. Their scope of clarity is narrow in the grand scheme of things. Important but narrow.

PMs don’t hire and fire. PMs don’t attend to people’s career trajectories. Product managers don’t mentor functions on their craft unless they manage other product managers. PMs don’t tell people how to do their jobs (or at least they shouldn’t). Product managers don’t pick tools. Product managers smooth over interpersonal conflicts, but leave certain things to team members and their managers. 

But if you are switching to people management—especially to managing a cross-functional team—you will need to unlearn this approach FAST.

In retrospect, I made a couple big mistakes:

  • Not realizing it would be a problem early on (despite it making sense in retrospect)

  • Not digging deep enough on an individual level first

  • Hoping that working together would be enough to smooth things over. Delaying taking decisive (but uncomfortable) action where it would be impactful and feasible

  • Paradoxically, my comfort level grappling with the white space of the product and the market, biased me against creating clarity for the team. It felt artificial

  • Assuming the care and concern I have as a product manager translates to care and concern in a management setting. Some of it does. Some of it doesn’t

  • Not quickly unlearning only having informal authority and influence. Formal authority is a different game, and one that carries a different burden

I’ve written “product management is not people management” hundreds of times over the years. But it took me getting back in the fray, in a complex situation with a cross-functional team (where I had/have depth in some areas but not others), for the message to hit home. 

For those considering the return after a long hiatus, I’d recommend holding as many things in this list constant as possible. Try to…

  • Stick to a functional team where you have all the skills required

  • Stick to more certain problem area (not something emergent and weird)

  • Stick to something with more stable career paths/patterns

  • Stick to something that is in motion already with momentum (no cold start)

  • If you need a cross-functional team, consider a different model (different functions reporting to different managers) and managing one of the functions

Hope this helps.

TBM 17/52: Decision Making vs. Decision Understanding

Big thanks to @ChrisSpalton for the review and drawings!

Two anglers wade in a river. One-hundred meters from each other. They complete each other's thoughts. I cast here. You cast there. I move here. You move there. Rhythmic casting, retrieving, and wading, pool by pool. 

"Did you see that ripple, over there," one angler says with a nod. "Yep," replies her friend (with a nod). They share a lot of knowledge and skills. They use the same words.  They know about rivers, this particular river, trout, these trout, the seasons, the hatches, fly fishing, each other, and so much more.

Decision making is fluid and almost automatic.

A couple miles away two PhDs at The University—a sculptor and a molecular biologist—are working on a project. What's happening? They take long walks together to learn about each other's world. New connections form. The theory of everything! Momentum! Then a temporary roadblock. Turns out artists and molecular biologists (or at least this artist and biologist) keep different schedules and have different uncertainty-level comfort zones. Quick, a proposal to "keep things on track!" Scientists are good at proposals, right? 

Alas, the artist has concerns and edits, and feels a pit in her stomach ("is this what I signed up for?") Motivation flags a bit. "Wait, are you still dedicated to this?" asks the biologist? Of course. More walks. More work. More collective sense-making. 

Decision making feels painful at times. Stilted. Circular. But over time, a wonderful partnership forms (and wonderful art springs to life).


There is no magic framework to operate like the two anglers. No magic metric. No template. No activity. The PhD students need to do the work and invest the time, curiosity, openness, dedication, and an open heart. The tough reality is that they also can't force it or rush it.  No human has an endless supply of the kind of energy. Our bodies/brains can only take so much before needing to recharge and DO something. To let our synapses make the connections they need to make—reinforced by action and motion. 

Sometimes we try and don't get there and have to try Plan B, C, and D. Heidi Helfand, author of Dynamic Reteaming: The Art and Wisdom of Changing Teams, shared this observation and wisdom with me:

When people come together in teams sometimes everything flows and it’s so easy. Like water in a river rushing along, moving around the rocks it encounters. Other times we bounce off the rocks and we might not even know why. But we get back together and press on and try to have a good life together at work. Sometimes I think it’s a combination of luck or something magical. When you have it you don’t want it to end. It’s some kind of chemistry.

Chemistry, work, mystery, and luck. And you can’t force it. That’s not easy. Do they teach mystery in business school? I’m not sure.

Drift and Understanding

Teams often talk about decision making challenges and what I call Decision Drift. Decision drift is when you decide something, but then your commitment drifts. Your team feels they are going back to the drawing board often. How are we supposed to fix decision drift? "Decide and commit!" Jeff Bezos tells us. "Identify the directly responsible individual!" says Apple. Run RACI. SMART goals. Roll out OKRs. 

I've come to see it in another way. Teams (and framework makers) focus a lot of attention on making decisions, but not a lot of time on understanding decisions and each other. There's a void in shared vocabulary, and a void in their shared understanding of implications and assumptions. And even when teams realize the issue, there's only so much cognitive "capacity" available to do the hard work to close the gap. Like the PhDs, you can't rush it. If you try, you can make it worse (something I’ve learned the hard way). Working remote during the pandemic has only exacerbated the problem. 

What might lead to decision drift? Why don’t people just call it out? Let’s focus on the humans involved, and their response to the situation:

  • Some people don't know what they don't know. They aren't sure about the implications of a decision. It seems fine, at least to them. My friend asks me, "do you want to go deep sea fishing?" That sounds fun! Get me on the boat. Two hours later I am seasick, chopping smelly fish guts.

  • Other people might have a sense that there are impacts that aren't being discussed. But they can't put it into words. It causes a slight discomfort. The discomfort is too small to motivate derailing the meeting. Example: you ask someone for directions and food advice in a foreign city. They seem knowledgeable but you have a hunch they didn't understand you. You don't want to waste their time, and they seem very generous, so you hear them out, thank them, and walk in the direction they suggested (but duck into an alley).

  • For some, their coherence "radar" is finely tuned. They sense the lack of coherence, and while they can't place it exactly, they sense the general vicinity. It bothers them, and becomes a bit debilitating. "I'm getting a funny feeling here I can't shake!" they remark. Queue up most horror movies to get a snapshot of this. No matter what they say, and no matter what they do, they can't shake it.

  • Perhaps it does not feel safe or worth it to “raise the flag”. The issues are clear, but sorting them out will involve energy you don’t have.

  • Or imagine a skilled deep-sea angler joins the two river anglers. Talking seems superfluous. Isn't this all figured out? Fishing is fishing. Can't we just fish? They spend their whole day shouting across the river and scaring the fish. Their friend feels alienated and quits fishing. Turns out fishing is fishing...but only at a high level. We routinely think things are more similar than different. Or more different than similar. 

  • Someone might be very skilled at communicating to people who "know nothing" about their domain AND people who only know about their domain. That's a unique skill--the connector--but not representative of all cross-disciplinary conversations. Can they see that? Or do they approach all situations with too much confidence?

There are hundreds of variations here. It is a heady mix of prior experience, assumptions, energy levels, patience levels, and practice. And changing context: a decision may be “final”, but the conditions shaping the decision are constantly changing.

So what can you do about it? 

How about goals and objectives?!

Goals may create some alignment. Seeing that point on the horizon is a start. But how you'll get there may be completely up in the air. The goal may be too lagging to feel actionable. Or too leading to feel flexible and accommodate the skills/expertise of the people involved.

Or the team manufacturers certainty for the purpose of setting a clear but overly generalized goals only to have the uncertainty creep up on them. Remarks Jeff Eaton:

[One reason for decision drift] is that in the face of uncertain futures, we build "account for everything" systems instead of flexible playbooks. This is a big issue when planning for rapidly changing/uncertain future needs; "predict a path and build for it," breaks down easily when the prediction isn't exactly right.

So yes, goals can help prevent decision drift. But they can also cause it. And at the end of the day a goal is a placeholder for tons of background and conversations. It is shorthand. It is a construct.

How about trust?!

A couple years ago I posted this image on Twitter. I believe in this message (and people seem to like it), but there’s more to it.

Teams often point to trust, and trust IS an issue in some cases, but I'm not sure it is that simple. Unless we create a highly transactional hand-off (e.g. "you do exactly X" and "I will do exactly Y") there will be drift. Things will happen that we don't expect. So perhaps it is less about trust, and more about decision boundaries. When we talk about trust, in many cases, what we are saying is:

Fishing friend. YOU stay in that POOL. OK?

Biologist! Send me the final rendered drawings of the cells, and I will create the sculpture!

If you stay in your lane, and I stay in my lane, and we each do the thing the other person can't understand, and we combine our stuff, we'll be good!

Congrats! You are the trusted, directly responsible individual.

Unfortunately, this way of working is much better suited to complicated problems, not complex problems. The trust we seek—if we even call it that—is not that easily attained (and not something we can will into existence). It certainly isn’t a “just”: “we just need trust!” Faith might be a better word actually…or trust in best intentions and our collective ability to work through it.

In other words, we may actually want and need the friction of the Trust=No route, albeit with the requisite safety and trust to work through it. At least at first. Our team may also behave as if “people don’t trust each other”, when mostly they just don’t understand each other. “We all care about psychological safety, and making this safe for each other. We just haven’t figured out how…yet.”

OK. What then?

Amazing things can happen when people from different disciplines work together. This approach is especially important for complex problems that benefit from diverse perspectives.

There's no magic framework that can instantly solve the problem. People require time to process—alone AND together.

They need safety to challenge their own assumptions and the assumptions of team members. To explore and dig. In our day-to-day, there is so much pressure to decide quickly. The end result is that premature converge makes decisions fall apart.

You need bandwidth and you can't rush it. When we rush to a plan, a goal, the RACI...what we are doing is creating PROXIES for understanding. Sometimes this will produce short term outcomes, but it is rarely what you need for lasting results. 

Take a break. Come back rested.

Work through professional culture clash.

Experience can help, but so does a beginner’s mind. If you’re very experienced, keep in mind that it might take a long time for people to catch up.

You need “doing”. Talking doesn't help after a certain point. It is important to shift your approach and change things up. Wade the river. Draw a molecule. 

Decision making is part “the making” and mostly “the understanding”. 

TBM 16/52: Goal Clarity (and Embracing Different Perspectives)

Huge favor to ask. Have you learned a new analytics product in the last year or so? If so, and you have 5 minutes to spare, I’d be very grateful if you could take this short survey. It would be a big help for my team.

Twelve people look at a proposed quarterly goal. They respond. Note the differences (you will inevitably encounter all of these in your career).

Person A looks at the goal and says "looks good to me!"

Person B looks at the goal and says “looks good to me!” But they are underestimating the difficulty of the effort.

Person C looks at the goal and says "that is not specific enough! There are so many ways I could approach that. Some I'm guessing you would not be happy with. Are you sure?"

Person D looks at the goal and says "OK this makes sense. Feels about right. But what is the bigger picture? If we achieve this, what will it enable? What is that goal?"

Person E looks at the goal and says "I'm a little lost. I'm not even sure where I would start. It doesn't feel actionable. It feels intimidating."

Person F looks at the goal and says "makes perfect sense as a longer term goal. But to keep us on track in the near-term we need something more leading."

Person G looks at the goal and says "that to is too specific! It implies a solution. I need something broader to work with."

Person H says "looks good" but doesn't look at the goal. They're sure their idea is great, and that when people see it in action, any discussion of goals will slip away.

Person I looks at the goal and says "looks good to me!" But they have an approach in mind that Person A, Person C, and Person E will hate. The goal didn't cover what was out of bounds. The team didn't surface their assumptions.

Person J looks at the goal and says "looks good! This is a good starter goal for the team. It isn't very impactful, and will change. But for right now this is fine. In the future they will use REAL goals!"

Person K looks at the goal and says "I don't have the energy to fight this battle. The goal makes no sense. And is incoherent with the work they are doing. But I'm done!"

Person L looks at the goal and says nothing. They joined a week ago and none of this makes any sense.

They are looking at the same goal. The lesson?

Goals do not magically create alignment. No two people see a goal the same way. It is impossible to bake everything into a single number or sentence.

To become more aligned the people involved need to:

  1. Work to build shared understanding. Have conversations. Discuss interpretations. Discuss how the goal will shape their decisions

  2. Have the safety to push back, rethink, discuss, tweak, and narrow

  3. Respect different experience levels

You are doing it right if you get a range of responses (even J and K).

And that's this week's post.

TBM 15/52: Stop Hiring Things to Do Too Many Jobs

Here's an anti-pattern to watch for:

Hiring a process, tool, framework, or label to do too many jobs.

An example.

A team starts using OKRs. You ask them "why have you decided to use OKRs?" They explain.

Well, the OKRs will help us set goals. Oh, and they will help us track our progress! Accountability, right? And alignment of course, and keeping score. Objective grading is part of it. And autonomy when a team sets good ones.

The way they work also lets you set stretch goals. Be audacious! It is all about learning and reflection, of course. Failure should be an option. Finally, if you get them right, they let you convey a clear vision to the rest of the organization.

That is lots of jobs. "Lots of bang for our buck!" you might say. I'm not so sure.

The problem with something that does lots of jobs is that it is very easy to send the wrong message. Say someone joins your company. Do they pick up on all the nuance? Do they know they can fail? Pivot? That it is about "keeping score" but in a healthy way? What exactly does "stretch" mean? "Wait, why are we using OKRs again? Does anyone even remember?"

This principle also goes for artifacts you might use at your company. I was in a meeting recently, and I watched as the team discussed a label given to a certain segment of customer.

I wrote down the various "jobs" for the label:

  • Targeting criteria for sales (e.g. target X companies)

  • A distinction for goal setting (e.g. "activate X orgs")

  • Segmentation to apply internal CSM/Support playbooks

  • A way to "size" our addressable market

  • Tool for prioritizing enhancements (e.g. "will this help X?")

  • A target firm-persona when thinking about design decisions

  • Strategy shorthand ("the X strategy")

That is 7 jobs. And I stopped counting. The problem? It is unlikely that the label will be effective at all those jobs. And very easy to attach even more meanings as newcomers get introduced to the shorthand. Communication is hard enough for even more narrowly defined concepts!

So here's the lesson. Always ask "are we overburdening this?" Think about running this test: if you asked "why are we doing this?" to ten people, how convergent would the responses be? Too much divergence? Narrow.

TBM 14/52: Discussing Complex Problems with Leaders

I have a book for sale! You can read it free here. Or download the ebook here. Or tip.


As a systems thinker type, how do you broach complex problems to leaders in your company? Note: I mention "leaders" below, but it is safe to say that most of us have a tendency to respond this way. Especially when we're under pressure.

Most leaders find the idea of a complex systemic issue threatening. There's no clear root-cause. There's uncertainty and unpredictability. And it is all happening on their watch.

So while you might think you're being helpful by presenting the issue (in all its nuance), it will not go over well. The leader will ask you for specifics. Who did what? Who said what? What should I do? They need information to solve the problem (one of dozens of problems they've heard about that day). They want a clear problem to solve, not a complex challenge to ruminate over.

What confuse them further is that you likely aren't just speaking for yourself. Empaths and systems thinkers often channel to needs of the collective. Meanwhile most of the people in their office that day have brought in specific problems and asks. In the back of the leader's mind they are thinking "I'm confused, what does this person actually want, and why do they care about this?" If you avoid specifics to respect people's privacy, and maybe even protect them, you risk the "so people are talking about..." problem. No one wants to hear "so people are talking."

So what should you do instead? As a card-carrying sponge these types of problems, I would never suggest you stop being you. I can go into my particular background in another post, but I've come to see this type of radar as a gift. It might have started from a not-so-happy place, but it is who I am. So be you 100%.

That said, it is important to get very clear on your goal. What do you want out of the conversation? What are YOUR needs in all this? What would be an ideal next step?

At least for me, I often feel a lot more comfortable talking about the needs of other people. Being a spokesperson. Channeling the pain/stress of others. I'm not as comfortable talking about my own needs (even when those needs related to others, e.g. "I want to feel my coworkers are safe and happy").

The problem with speaking for people, is that you will be much more likely to elicit a threat response. And you're liable to misrepresent their perspective, or even undermine their efforts.

I've found (recently, it took a long time) that I can be a lot more effective if I:

  1. Speak about my own needs, and my response to the situation. This can be a big step.

  2. Have an ask in mind. This doesn't mean having a "solution". A next step will suffice.

  3. Have an ask ready for the person I am speaking to. What do I want THEM to do?

  4. Consider the role I want to play in this. What responsibilities do I want to take on?

  5. Work to create safe spaces where other people can try to voice their own needs (vs. proxying).

  6. If the problem is thorny and complex, with lots of moving parts, try to focus in on one moving part as a starting point.

  7. Consider safe-to-fail experiments beforehand. Your first experiment could be facilitating a conversation with more people and the leader.

  8. Put myself in the shoes of the leader (e.g. this being the tenth conversation about problems so far today).

Hope this helps.

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