225: What Should We Talk About?

Every client approaches their coaching sessions differently.

Sometimes what we talk about is obvious—there's a burning problem that we need to discuss ("our biggest customer is pissed off and threatening to leave") or important updates that need to be shared ("our team offsite made me rethink our long-term strategy")

But sometimes it's less obvious what would be the best topic to explore in a given session. So today I want to provide a framework how to make the most of a coaching session with me or any other coach / advisor / trusted thought partner.

GIGO: You get what you put into coaching

As a coach, I've seen that the most impactful sessions result from the client being intentional about what they want from the experience—while being open to following where the discussion leads. Your coach can't read your mind. If something big has happened or is weighing on you and you don't bring it up, your coach might notice something is off, but may not be able to draw it out of you as quickly as if you proactively bring it up.

Preparing yourself and your coach

Taking a few minutes before each session to reflect on what you want to discuss can dramatically increase the value you get from coaching. One of my clients sends an agenda a few hours before our call which helps me understand his context and mindset so I can mentally account for how we'll spend the time. Even if something else comes up during the session that feels more urgent, having this preparation helps ensure you're making the most of your time together.

Here's a list of potential topics to bring up:

1) External obstacles to your most important objectives

Sometimes shit hits the fan. Your coach can help reel you back from the anger, sadness, anxiety, and fear that's flooding your system and figure out how to stop the bleeding. Whether it's a key employee quitting, a failed product launch, or a major customer crisis threatening your business, these situations can feel overwhelming, and it's easy to spiral into worst-case scenarios. Your coach can help you take a step back, process your emotions, challenge any catastrophic concerns, and develop an action plan to fix the situation.

2) Major conflict with an investor / senior leader / employee

There's everyday friction and then there's growing frustration and resentment that could get really bad if not addressed. You disagree with your co-founder about the direction of the company, your investor keeps pushing for growth at all costs, your head of sales keeps missing targets but always seems to have an excuse. Your coach can help you understand where things went wrong, make sense of the other person's behavior, find the root of the issue, and provide ideas for how to resolve the situation without making it worse.

3) An important decision that needs to be made

Whether it's firing an employee, choosing the right partner, or setting a major goal, your coach can help you identify the why behind your decision, articulate the key considerations, generate and evaluate options, and make a plan for deciding. Sometimes this means acquiring more information or consulting others before making the final call—and possibly setting a deadline to do so.

4) Accountability to a long-term plan

If you are working towards something big and challenging—cold outreach, a big fundraise, working through a hiring process—your coach can help you stay focused and motivated. Putting a plan together and reviewing it each session can help you get a dopamine hit to keep you going, troubleshoot any issues, and rework the plan when things get off track. Sometimes founders get so focused on the end goal that they forget to acknowledge their progress, leading to burnout and demotivation. Regular check-ins create a rhythm of reflection and adjustment, ensuring you're not just moving forward, but moving in the right direction.

5) Bad habits or self-sabotaging behavior that are holding you back

This is a tough one to admit but if you find yourself avoiding difficult conversations, falling back into video games, doomscrolling, or skipping the gym, you should bring it up with your coach. There's probably something that's bothering you and keeping you from engaging with these activities that "you know" are important but aren't doing. A good coach should be able to help you make changes to your behavior without shaming or judging you.

6) Nagging questions or negative patterns of thoughts

Even the most confident founders, in the quiet of a late hour after a long day, sometimes thinks to themselves "Am I really good enough to do this business?" or "This idea is never going to work and I should just quit now". These doubts and fears, if left unaddressed, can fester and grow into paralyzing self-doubt, so it's important to bring them into the light and examine them with your coach. Your coach can help you zoom out and look at what's really going on beneath the surface. Often, there's a belief or assumption you're carrying around that's causing you to repeat the same mistakes or stay stuck in the same situations.

7) Feeling lost or overwhelmed

When everything feels urgent and important (or nothing does) it's easy to get stuck in analysis paralysis or a cycle of reactivity rather than strategic action. Your coach can help you step back from your swirling thoughts to identify a meaningful, interesting, and maybe even fun course of action. Your coach can also help you map out your priorities across different domains (team, product, health, family), break them down into manageable next steps, and create a realistic timeline that aligns with your vision and resources.

Directing or redirecting your coach during the session

If you want to make sure there's time to discuss something else in the call, flag it to your coach. If the conversation is going in an unproductive place, let them know. One of my clients is really great about letting me know when she's not getting what she wanted from a given direction and for us to switch gears. A good coach will appreciate your directness and adjust their approach accordingly to better serve your needs.