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My essays, thoughts and presentations on product management and strategy

My collection of essays, thoughts and presentations

How I coach myself - Learning lessons and making real changes

The most career limiting thing you can do is to fail to grow. The skills and behaviors that lead to promotion and success early in your career are rarely, if ever, the ones that lead to success later in your career. Yet successfully developing over time can be incredibly difficult as it requires undoing old behaviors.

As an example, early in my own career in engineering I felt like the most important thing was to be technically brilliant, the smartest person in the room and to push the team to deliver the ‘perfect’ solution. I got great performance reviews but ultimately people didn’t want to work with me, one even called me ‘caustic’. To grow I needed to adopt new behaviors.

Since then I’ve spent a lot of time developing myself and coaching teams. Over that time I’ve found a couple of tools incredibly useful for self development, below are all of the details. Towards the end I describe my favorite approach, sending notes to my future self, and share a Google Sheet tool that makes it easy to implement.

Career steps map to behaviors

Before I dive in to methods for developing behaviors it’s important to frame how and why successful behaviors tend to change over the course of a career. For many people in the tech industry their steps will be roughly: individual contributor, leading a small team, then gradually increasing scope until they run a significant department. Here’s a simple 3 phase model for that career path:


Phase 1 - Depth and Effectiveness - When you are an individual contributor you are mainly rewarded for efficiently and effectively getting things done. This career phase is about depth and the ability to enable your department to move faster and be more successful. You need deep competency and task efficiency to succeed here.

Phase 2 - Enabling and Coordinating - When you are leading a small team the focus shifts to enabling your team, helping them grow and coordinating with other teams in your department. You need coaching, collaboration and influencing skills here.

Phase 3 - Strategy and Process - As your seniority and scope grows, you are increasingly rewarded for how your group shapes and contributes to the overall business strategy, hiring and growing leaders to build a high performing department, and cross-department collaboration to make the whole company more aligned and successful. You need strategy, process management, general management and communication skills to succeed at this level.

As you can see from the phases and the diagram, the behaviors applicable in each phase change significantly. If you over-use the successful behaviors from an earlier stage that is not simply redundant, it’s harmful. For example, deep technical competency in the team leading phase can cause you to be too directive with your team to allow them to grow. 

The development paradox

Even when you recognize the behavior change that’s needed it can be extraordinarily difficult to enact it because your success has trained you through a long term positive reinforcement loop. 


Breaking out of these behaviors and bedding down new behaviors requires a different reinforcement loop. Fundamentally you need to observe your behavior, identify where a different behavior would be a better option, enact that behavior, then observe the results.

Here’s that framing from the example early in my career I mentioned earlier:

  • Observation: A teammate in an engineering team proposed a non-optimal solution for a problem. I told them that was crazy and that I knew there was a better solution. I pushed them hard to adopt my approach since it was clearly better and would save time in the long run

  • Identify: While the specific solution may have been better, I was not collaborating with my teammate and working towards shared understanding. The person came to resent me and at one point called me ‘brilliant but caustic’. The short run solution I forced was OK, but the team was weaker in the future

  • Enact: When working with teammates the goal is to lift each other, not disable each other. When someone proposes a ‘wrong’ solution work together to understand where they are coming from and why the proposed solution may be best for now. Over time develop shared understanding of the problem space, what you’re building towards and the technology that might help so you don’t have to conflict at solution time

It’s easy to observe that contradicting a team mate isn’t ideal, but I had forged an engineering career by building ‘brilliant’ solutions, so it came so naturally I found it hard to resist. That behavior had to go.

The hardest part of self-coaching is generally in enacting the new behavior when you encounter the situation in future since we tend to respond to situations automatically based on our prior experience. 

How the hell do you observe and correct yourself?

It's not easy to observe yourself, identify better approaches and make long term behavioral change. For a long time I used a career coach, that I met with weekly or bi-weekly, to help me through the process of constantly examining my behavior and training myself to recognize triggers and the response I wanted. 

Coaches are awesome and I'd highly recommend them but they're expensive and more importantly, they only get to work with you periodically. I realized that I was always observing my own behavior and considering change, I just didn't have a better framework to enact it. I needed a mechanism to sit on my own shoulder and nudge myself. 

There are two tools I’ve found helpful for that nudge, the diary method and the reminder method. 

Tool 1. Diary Method

In the diary method I reserve some time either at the end of every day or at the end of every week to reflect. I tend to note:

  • At least 3 things that went well

  • At least 3 things that didn’t go well

  • Focus areas for next week / tomorrow

For the ‘3 things that didn’t go well,’ I spend some time thinking about how they could have gone better. If I’m not sure of the best way to have handled the situation, I do some research to look for new approaches. Once I know how I would have liked to handle it, I generally write a note in the form: what happened, why was that problematic, what I should do to better handle that situation in future or now if the situation is ongoing. When considering the what piece, it’s important to think deeply about how the sub-optimal events happened. How were they triggered? Why does that trigger cause that outcome? Spending time thinking about the trigger will allow you to more easily spot the trigger in future and prevent falling in to default behaviors.

This approach is very helpful as you start new positions, begin collaborating with new teams or implement new processes. The challenge is that it can be hard to take the time to reflect in this way and regular reflection is key to generating real change since it primes your brain to recognize the situation in future. For this reason I recommend blocking time in your calendar and trying to do it daily rather than weekly. If you do it daily it is far more likely to become a habit.

Tool 2. Reminder method - aka Notes to my Future Self

My favorite method for self development is to send ‘Notes to my Future Self’. My notes are in the form of emails that I’ll receive in the future that will remind me of the lesson I’m aiming to learn. The notes are usually in the form of what happened at some learning moment, why that was problematic and what I should do in that situation in the future. The goal is to remind myself of the lesson and reinforce the learning so that next time I encounter the situation I’ll recognize it and respond differently. 

I set up the notes so that lessons I’m trying to actively bed down get emailed to me frequently whereas lessons that have become pretty ingrained are sent infrequently to just refresh them in my mind.

Here’s an example note to my self that’s currently in rotation:

The problem: Awful meeting with XXX where they did not feel heard on YYY design (YYY is a broad area that cuts across the product space rather than being a single functional area)

What happened: I pushed hard to chunk the work in to functional areas and distribute it across teams, XXX did not feel heard because (a) there was no clear owner for discovery of all of the pain in YYY across the company, (b) there was no way to go about discovery, (c) there were no experts in the room to help.

Jumping in to solutions didn't help, need to find a way to do cross company discovery?

What should happen: Launch discovery programs, nominate cross squad discovery owners, map discovery programs in to overall product planning

In some cases, instead of lessons learned through an event in the past, the notes reference great frameworks, methodologies or approaches I’ve read about. In this case the goal is to remind myself that I intended to add them to my body of knowledge and reinforce the memory of the tool and when I intended to use it.

Here’s a real life example that’s currently in rotation:

Tool: Time spent pie chart,

When to use it: Product Managers often struggle to spend enough of their time focusing on important activities such as strategy creation, competitive analysis, customer engagement and product discovery. This pie chart approach is much simpler than calendar audit approaches I've used in the past"

I have over 45 notes to myself active right now, some returning frequently, others very rarely.

I’ve implemented ‘Notes to My Future Self’ in a variety of ways over the years including Boomerang for Gmail and using the newer Gmail send-later and snooze features but I’ve found those approaches to be clunky. 

More recently I’ve used this simple Google Sheet with some embedded Apps Script that emails notes to myself every night. The sheet is super simple, each note has a subject and body for the email and a frequency.

The body is often in the form ‘What happened:’, ‘Why that was not optimal:’ and ‘What should happen in the future’.

The frequency is the average number of days between emails to myself for this note. The actual reminders for each note happen randomly so they approximate the frequency. This element of surprise is important. Since the notes aren’t delivered on a detectable cycle my brain gets used to I’m much more likely to truly reflect on them rather than skimming and deleting them.

When it works you’ll know

I’m a big fan of collecting as much 360 degree feedback as possible and the changes in the feedback over the years I’ve been using these techniques are incredible. Some of the most strident feedback from 4 to 5 years ago has gone from an area of improvement to being behaviors I get complimented on. 

I’m still growing as a person but I hope these techniques are as helpful for you as they have been for me. Please feel free to use / share the Google Sheet for sending ‘Notes to My Future Self’. 


My thanks to Brian Balfour (@bbalfour), Sidharth Kakkar (@sikakkar) and Sharon Shi (@shartron) for reviewing earlier drafts of this post

Shaun Clowes