Bonus: some practical tips

How to work with detractors, find thought partnership, and more

I hope the three tools I’ve outlined help a bunch. Here are a few more tidbits I’ve picked up over the years of making hard team decisions.

1. Find your thought partner.

Most tough decisions will involve a group of stakeholders. There might even be a few levels:

The review group / brain trust: stakeholders from across the company who care about the decision or provide relevant expertise.

The working group: a handful of people who are closest to the decision and partner to drive the decision making process. If the review group is large, make sure to have a smaller working group to be able to make faster progress.

Other stakeholders: There could be more levels depending on the size of the company and gravity of the decision.

But being the driver of a big decision is not only challenging, it can be incredibly lonely. It’s easy to feel insecure — am I being assertive enough? Are others feeling heard enough? Is there anything to this crazy idea I had in the middle of the night?

The feedback loop with the group is often too slow.

I’ve found that for especially tough decisions, you need a thought partner — singular. One person who is right there with you. The best thought partnerships feel almost like a mind meld. You share all the same context. Any new information, you both see and talk about. You debrief after every broader discussion. You are Slacking each other thoughts as soon as they come into your head. There is complete psychological safety for being honest and sharing crazy ideas — sharpening thinking, building on ideas, bringing you back to reality when that’s needed. For me, this is often a designer, a fellow PM, or sometimes a product-oriented engineer.

Great thought partnerships reduce the feedback loop for how you iterate towards a decision to almost real-time, challenging your thinking, adding new perspectives, and generating sparks of genius along the way. No ego. No rivalry. Both of you are just trying to get to the best decision together. They require complete transparency and no holding back.

Especially for tough decisions, whether or not you have a great thought partnership can make or break the process.

2. Embrace detractors.

When someone seems to just be against my process or proposal, it’s very easy to want to pull back from them or dismiss their feedback. I'm the kind of person that hates confrontation, so sometimes I like to pretend that the conflict doesn’t exist and hope things will just work themselves out. Disagree, and commit dude.

You can’t always convince every detractor, and that isn’t the goal. It’s less about convincing and more about the detractor feeling heard. Often times detractors have some information that they feel you aren’t considering. When you send a quick Slack after the meeting or meet with them 1:1 where it feels personal, guards go down and you can have a productive discussion. In some cases you end up being more aligned than you thought or end up with a nugget of insight that can benefit the proposal.

But even the worst case has a good shot at being productive: the other person may not agree but at least feels heard, understands you are running a thoughtful process with hard tradeoffs, and is much more likely to support the end result.

3. Communicate where you are in the decision making process.

At Coda, we have four stages that describe our process:

Wallow: Idea and problem statement generation. These are inputs to the frame.

Frame: Synthesize the questions and options. This is where the frame matures into the top question and set of options.

Propose: Pick one of the options. This is where the frame is narrowed to its conclusion.

Close: Commit and execute. Get your team’s buy-in and move forward!

Our CEO, Shishir, covers this in detail in his

Eigenquestions⁠

doc but whatever process you use, it’s important to communicate where you are at.

For me, that means making sure that if something is in the brainstorming stage, everyone in the meeting knows that “this is a wallow” — no bad ideas, divergent thinking welcome, “yes, and” please. Otherwise, you can end up spending too much time debating details that don’t matter yet and killing ideas in their infancy before they have time to mature.

If I’m in the “propose” stage, I also need to make that clear. We are converging on a solution, so let’s not open up Pandoras box with open brainstorming. Otherwise, you can end up in tangential discussions instead of driving towards a decision on the proposal.

To be clear, sometimes I realize during a meeting that I may think we are in the “propose” stage, but a lot of folks are skeptical that we are asking the right questions, let alone arriving at the right solutions — so I may have to evaluate going back to the frame stage, and that’s a healthy debate to have with the group. But having clarity on what stage feel you are in will allow stakeholders to give the right input at the right time.

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That’s it! If this doc has been helpful, or if you have some tips or tools I should add to the list, please hit me up on Twitter (

@jerols⁠

). And if you like to get emails, I have a newsletter too:

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