You need a thought partner
As you move up in your career, you need a thought partner – but most people aren't good at it naturally. Here’s how to coach your colleagues (or AI) to act like one.
👋 Hi, it’s Greg and Taylor. Welcome to our newsletter on how to make high-stakes professional and personal decisions in your 30s.
When I first started working with Greg, he drove me nuts.
When I brought him a challenge or question, he’d often turn to a white board (at the time, we were in person in NYC) and move the conversation backwards.
He’d use the white board to scope out different scenarios and play out unintended consequences (or upsides). He’d question my assumptions, dig into a thread that piqued his interest, and ask me what else I’d considered.
Like I said, it drove me nuts. But over time, I realized these conversations were making my work better. He was helping me avoid mistakes before they happened, and building my business acumen as we went along.
This is what a thought partner does.
People are constantly talking about mentors – how to find one or how to be one. But I don’t want a mentor – I want thought partners (many of them). People with enough context to help me solve the challenges I’m facing, but enough objectivity to check me and force me to evaluate multiple angles.
Here’s our guide for how to identify a great thought partner, encourage thought partnership in your network, and be a great thought partner to others.
– Taylor
Why you need a thought partner
As you move up in your career, you get handed bigger, stickier problems.
Most of these are hard to solve on your own, and it can be really lonely to try. We’ve both spent hours spinning over a problem, when really what we needed was a 30-minute conversation with someone we trusted to get unstuck.
This is a thought partner – someone with enough context to help you sort through a big problem, who can bring some objectivity, help you zoom out, and push you to think of other angles.
Let’s be clear: a thought partner is NOT:
A mentor. This is usually someone older than you, who will impart “how they did it” when they were at your stage. (We think they’re mostly useless – more on this in a future post).
A work best friend. A work best friend is there to commiserate and tell you, “Ugh, that’s so annoying.” They can be a thought partner, but they often aren’t.
A cheerleader. A thought partner doesn’t say, “You can do it” or “I’m sure that will work.” The opposite – they often point out why something might not work.
What a good thought partner does
At the highest level, a good thought partner helps you process a problem and work your way toward a solution (even if they don’t necessarily “solve it” for you). A thought partner:
Digests the context of the situation you’re facing. Either they’re already close to the problem because you work together, or they have enough context (usually from having faced a similar problem before) to get familiar quickly.
Plays out various scenarios with you. They talk through the options in front of you and help you weigh the risk/reward of each. If they’re good with numbers, they probably open Excel or start writing on a whiteboard (we call this “napkin math” – learn how to do it here).
Suggests options you haven’t thought of. They don’t say, “You should just do it this way,” but they do point to an Option C that you weren’t considering.
Pushes back on assumptions. A good thought partner will help you pressure-test the assumptions that underlie your decision. A thought partner recently said to me, “You say this is a high customer priority, but that customer only has a $5,000 contract with us – are they worth it?”
Helps you anticipate long-term effects and reactions. We tend to downplay the risks of the options we like, and overstate the upside. A good thought partner helps you think more clearly about the long-term risks and rewards of each option.
5 reasons most people aren’t natural thought partners
A thought partner sounds great, right? But most people won’t do all of the above without some coaching. Here’s why:
They’ve been taught to have “the right answer,” so they’re uncomfortable sitting in ambiguity or admitting they don’t know. They’ll rush straight to providing a recommendation even if they don’t have all the context.
They think you’re asking them for advice. They’ll tell you, “This is what I would do” because they think that’s what you need from them.
They think you want validation. So they’ll pat you on the back and say, “I’m sure you’ll get it right,” thinking that they’ve made you feel good about yourself.
You’re not giving them enough context. You’re anxious about showing that you don’t know the answer, so you’re not giving enough details for them to really dig into the problem.
Secretly, you do just want the answer (not the process to get there). Deep down, you may just want a wise figure to say, “This is exactly what you should do.” If that’s what you want, you won’t encourage the back-and-forth necessary for a thought partner to succeed.
How to coach people to be a good thought partner
A thought partner isn’t like a mentor – you need more than one. You should be coaching multiple people on your team and in your network to act as thought partners, so you can bring them problems that require different expertise and contexts. Here’s how to do it.
Build a “bench” of thought partners you can pick from. Don’t rely on one person for everything – build a bench of people with different contexts and expertises. That should include people from your team, same-role counterparts at different companies, and trusted friends.
Tell them that you need a thought partner. Be upfront and tell them you’re not looking for advice – you need someone to work through the problem with you. Here are phrases we use to signal this:
✅ “I want to think out loud about this problem for a few minutes.”
✅ “I want to pick your brain on something I’ve been grappling with.”
✅ “Let’s riff on this problem for a little bit.”
✅ “I’d like to whiteboard a few options with you.”
✅ “I’m not looking for the answer … let’s just tease out the various paths.”
Give them enough context to be helpful…but no more. Send a pre-read, even if it’s just a short email outlining the problem. If you can’t, spend 5 minutes outlining the problem for them, including the challenge, initial data you’ve gathered, possible options to solve it, and the assumptions that drive those options. Do this quickly and then let them ask questions.
Ask specific questions. If you’re not getting what you need out of your thought partner, start asking questions. Things like:
✅ What am I missing here?
✅ What upsides do you see to this solution? What downsides?
✅ What do you assume would happen next if I go down this path?
✅ What would you do differently?
Don’t shut them down when they push back. The biggest mistake people make with a thought partner is getting frustrated with their suggestions and shutting them down. This is understandable – they won’t ever have as much context as you, so they’ll inevitably suggest things that won’t work or that you’ve tried already. But sit and listen anyway – you only need to push back if they’re hell-bent on a solution you have concerns about.
Phrases that shut down a thought partner conversation:
❌ “I already tried that and it didn’t work.”
❌ “I don’t have the budget / resources / bandwidth for that.”
❌ “That will never get approval / my boss won’t like that direction.”
Need a thought partner in a pinch? Use AI
We use AI as a thought partner every day, and we think the best LLMs go toe-to-toe with humans as far as strategic advice.
That’s because AI is an expansive thinker – it can give you as many options as you need, and dig into each of those options without getting tired or grumpy. We ask Claude to review our board deck before every board meeting, and its feedback is almost identical to our world-class human board.
Here are our tips to use AI as a thought partner:
Use Claude over GPT. Claude is the best “strategic thinker” of the bunch and is able to understand and predict the bigger implications of small decisions.
Tell AI how to act. Say, “I’d like you to review this deck and give me feedback as if you’re my CFO, and your focus is meeting our revenue targets while staying within our budget.” Then do the same thing with other roles and other focuses.
Try the voice feature on the GPT4 mobile app. It can be easier to have a back-and-forth conversation out loud – you’ll naturally censor yourself less.
Our advice
Mentors are nice. Coaches, especially if the company is paying, can be great. Therapists can help sort out the past. But thought partners raise the level of your game. Thought partners make you smarter, more balanced, and more nuanced.
To take advantage of them, you need to a) keep YOUR ego in check – be willing to adjust your original plan or POV and b) coach your thought partner to be a good one – especially as many people have not done this before.
Don’t look for one magic thought partner who can solve all your problems. Like a mentor, these are hard to find and rarely available to you all the time.
Instead, train yourself to train people to be a good thought partner to you.
To the next 10 years,
Greg and Taylor