Coaching to a destination

Micaela Shaw
7 min readNov 29, 2022

Many leaders say they want to help their people grow, but actually acting on this is difficult if they haven’t taken the time upfront to understand where people are coming from, and what they want to grow into.

“Where do you think it comes from?” said a voice in my earbuds.

“Where does what come from?” I said.

“The chip on your shoulder. You seem to think people are always underestimating you.”

These words from my executive coach stopped me in my tracks. It was 2016 and I was walking through the interior desks of our Philadelphia office towards a conference room, having just gotten off a train. I stopped, hurled my heavy bag onto an empty desk and slumped into a chair.

At first I bit back a defensive answer. There was a lot baggage in that question. I was bullied as a kid and always felt like I had something to prove.

But the first answer that reached my lips was this. “I’m not sure they know where I’m coming from, or where I want to go.”


The thing is, I think a lot of people feel this way.

And as much as managers say they want to support their people and help them grow, many don’t spend the time to understand what destination they’re coaching their people towards.

That day I decided that while it was going to take time for me to solve this for myself, I was going to be proactive about not replicating the problem for people who reported to me.

Since 2016, I’ve had over 15 career alignment sessions with direct reports. These are formal listening sessions where I take the time to start off working relationships on the right foot.

As a leader, I want my people to feel like I care about where they’ve come from and where they want to go. And taking the time upfront to do this has made a tremendous impact on my ability to effectively coach people.

Setting Aside Time

Everyone has their own style of getting people to open up. My husband is one of those people who can get airport security guards, birch trees and lamp posts telling him their life story in a minute flat.

I’m not naturally great at this. People tend to hold me at arms length for longer. I present myself with a buttoned up formality that opens up to wooly sweater only as people begin to hear stories of my pie-in-face parenting skills. The teams I work with also tend to be incredibly driven and focused on jobs at hand. So it’s easy to skip over getting squishy and vulnerable and just get up to our elbows in the work.

So for me, setting aside real time to talk about who my team members are and what they want is essential. And I mean real time. Like 3 hours. Ideally offsite and in person.

Set the session up about 90 days into working together. This will seem like a big chunk of time, but you don’t want to rush this conversation. I recommend 90 days because you need some context for each other’s communication style.

Before this session, you’ll need to have your team member’s most recent job description and (optionally) a personality test. (They can take a free Meyers Briggs one here at 16Personalities. Some people hate personality tests, so skip if they hate them. It’s literally just a proxy to get them talking about how they see their personality.)

Your meeting invite can look like this:
Title: Career Alignment Session

Description: Now that we’ve been working together for a few months, I’d like to spend some time learning about you, your communication style, your role and your goals. This will help me be a better leader to you.

Our time together will be broken into three sections:
* About You/Working Preferences
* Current Job Description Review
* Goals/Future Job Description Vision

This will mainly be a listening session on my part but at the end of the session, you’re welcome to ask me back any of the same questions. No need to prepare anything in advance, but I’ve attached questions in case you’d like to think about them.

Questions to Ask

Each question block should take 30–50 minutes. Take time for breaks in between. And don’t worry if you don’t make it through every question. Feel free to ask follow-up questions where relevant. If your teammate is comfortable with it, it may be helpful to take some notes. But as a manager, you need to prioritize being an excellent listener throughout the entire session.

About You/Working Preferences

The goal here is to understand where your team member is coming from and what they are looking for in a leader. This is your chance to uncover the instruction manual for how to be an excellent boss to them. It’s also your chance to uncover sensitivities that you may have been entirely blind to without asking. It’s important to state in this section that they should only share what they’re comfortable with. The goal is to uncover helpful context for your working relationship and not to pry.

  1. When you took the personality test, how accurate did you find the results? What rang true? What rang false? How does your personality impact where you tend to excel at work?
  2. Tell me your story. How did the way you grew up shape the professional you are today?
  3. Tell me about a manager, coach or teacher who helped you grow. What did they do that you found effective?
  4. How do you like to receive positive feedback? How do you like to receive negative feedback?
  5. Tell me about a team member you worked with in the past who you didn’t naturally see eye-to-eye with. How did you address the situation?
  6. How do you learn? Do you prefer to read information, hear information, visualize information or something else?
  7. What’s been the proudest moment of your career so far?
  8. What are some rules for our team that you’d like to see us enforce?

Current Job Description Review

Particularly when you’ve inherited a new team member, it’s really common for them to have 1) an outdated job description 2) a job description that doesn’t accurately describe what they do 3) no job description. This is an opportunity to learn where they feel like their job description is wrong and what they think it should be. For new-to-company team members, 90 days is a good time to get their take on work that they believe should or shouldn’t be a part of their job, but wasn’t in the original job post.

  1. Taking a look at this job description, how aligned is it with your day-to-day work?
  2. What’s missing?
  3. What is in here but you’re not doing currently?
  4. Are their any resources you need to fulfill this job description that you’re missing?
  5. Over the next 12–18 months, is their anything in this job description that you’d like to stop doing?

Goals/Future Job Description Vision

This is often the hardest part of the conversation for your team member. They might feel insecure about admitting that there are areas where they’re not as sharp as they’d like to be. They don’t want to seem disloyal by admitting that they could see a career outside your company. They don’t want career ambitions to seem outlandish. If you can get through this conversation though, it opens the door to getting comfortable talking about a learning agenda and talking about dreams. Helping your team member visualize where they want to grow and go is the first step in helping them get there.

  1. Over the next 12–18 months, how would you like to see your job description evolve?
  2. What would you like to learn at work in the next year?
  3. What are the parts of your job that you want to keep doing throughout your career, regardless of whether you stay at this company?
  4. What other companies or industries are you interested in learning more about?
  5. Is there anyone (on LinkedIn, in your network, in your community, at this company) whose job you would love to have someday?
  6. What do you want to be known for professionally?
  7. Are there any people at this company or in my network who might be able to help you learn?
  8. Are there any projects that you think would be helpful to your growth in the next year?

Wrapping Up

Thank your team member for their candor and openness. It takes trust to have these conversations.

Ask them if there’s any questions you asked that they’d like to hear your personal response to. You should be prepared to be honest and candid with them in exchange.

Hopefully after this conversation, your team member feels like you get them. However, the month following is where you really need to show them you were listening. As a follow-up, try to identify some behaviors you’ll commit to as a leader and some connections or experiences you’ll expose them to over the next 3-6 months. Then bring what you’ve learned into 1:1s and your working relationship.

While a career alignment session isn’t designed to be a conversation about promotion, it can create a foundation for such a conversation. If you identified a specific future role that your team member may want to work towards, partnering on a Vision Job Description can be a great next step. This will help you have a conversation with them about any gaps in their current skill set and begin to socialize the idea of promoting them internally.

It’s also possible that you identify that their career ambition is not a role that will exist at your company. In this case, consider whether there’s a way you can help them find such a role at a different company eventually. If you are serious about being a leader who helps people grow, you shouldn’t be precious about whether or not that growth is at your company.

At the end of the day, great coaches need to do the following:

  1. Communicate with players in a way that helps them learn and inspires them.
  2. Understand their players strengths and weaknesses to put them in the right positions.
  3. Help their players visualize what success like.
  4. Identify skill gaps and expose players to opportunities to build new skills and strengthen weaknesses.
  5. Take risks and provide opportunities for players to grow and discover new strengths.

However you do it, understanding where a player is starting is key to playing the role of coach effectively.

The bonus? Actually getting to know people who work for you helps you develop lifelong relationships with team members that you’ll take with you long after your role of their manager is over.