FAQ

• New Managers/Leaders

• Veteran Leaders & Growth

• About the Relationship

• Practical Concerns

How do I transition from being "one of the team" to being the boss?

This is one of the most common challenges, and there's no single script for it. What I've found is that the transition happens differently for everyone depending on your relationships, your communication style, and what you value most.

In our work together, we'd explore what this shift means for you specifically. What parts of your peer relationships do you want to preserve? What boundaries feel necessary? Often people discover that the discomfort comes from assumptions about what a "boss" should be rather than who they actually need to be for their team.

The goal isn't to become someone else - it's to find your authentic way of leading people you used to work alongside.

How do I give feedback when I've never done it before?

Feedback feels scary because we've all received bad feedback at some point. The good news is that feedback is fundamentally just communication, and you already know how to communicate.

Rather than learning a formula, we'd explore what makes feedback feel difficult for you. Is it fear of conflict? Uncertainty about your authority? Worry about damaging relationships? Once we understand your specific hesitations, we can work on building your own approach to feedback that feels genuine to you.

Most people discover they already have the skills - they just need permission to trust themselves and practice in a safe space first.

What do I do when a former peer now reports to me?

This situation brings up all sorts of questions about loyalty, fairness, and identity. The answer isn't the same for everyone because every relationship is different.

We'd explore the specifics of your situation: What's your history with this person? What are you worried might happen? What do they need from you now that the relationship has changed? Sometimes the conversation you're dreading is exactly the one that clears the air.

What I can tell you is that avoiding the awkwardness usually makes it worse. Finding your way to address it directly, in your own words and style, almost always helps.

How do I balance being liked with being respected?

This question usually reveals a deeper assumption: that you have to choose. But in my experience, that's a false choice that limits you.

We'd explore what "being liked" and "being respected" actually mean to you. Often people discover they're worried about something more specific - like being seen as harsh, or being excluded, or losing connection with people. When we name the real fear, we can work with it.

The leaders who struggle most are usually the ones trying to be someone they're not. The ones who thrive have found ways to lead that feel authentic to them. That looks different for everyone, and that's exactly as it should be.

Is it normal to feel like an imposter in this role?

Absolutely. Almost everyone feels this way when they step into a new level of responsibility. The imposter feeling is actually a sign that you're stretching yourself, which is exactly what growth requires.

What we'd explore together is: What specifically makes you feel like an imposter? What evidence are you ignoring that suggests you do belong here? What would confidence look like for someone with your particular strengths?

The goal isn't to eliminate the feeling entirely - it's to understand where it comes from and develop your own relationship with uncertainty and growth.

How much should I be doing vs. delegating?

This is one of those questions that doesn't have a universal answer. It depends on your team's capabilities, your organization's needs, your own strengths, and what actually energizes you.

We'd look at what you're currently doing and why. Often people hold onto tasks for reasons they haven't examined: control, perfectionism, guilt, or simply habit. Sometimes they delegate things they should own because they're avoiding discomfort.

The work is figuring out your own decision-making framework - one that serves both you and your team. That framework will be unique to you and your situation.

How do I handle someone who isn't performing without being mean?

The fact that you're worried about being mean tells me you care about people, which is a strength. But it might also be limiting you.

We'd explore what "being mean" means to you and where that fear comes from. Often people discover they're conflating clarity with cruelty, or honesty with harshness. They're not the same thing.

Avoiding difficult conversations doesn't protect people - it actually denies them the information they need to improve. We'd work on finding your way to be both honest and humane, in a way that feels true to your values and communication style.

How do I know what kind of leader I want to be?

This is actually one of the most important questions you can ask, and it's deeply personal. There's no leadership template you should be trying to fit yourself into.

In our work together, we'd explore who you are, what matters to you, what energizes you, and what kind of impact you want to have. We'd look at leaders you admire and why, and also at leaders you don't and what that reveals about your values.

The answer emerges through exploration and experimentation. It's not something I can tell you - it's something you discover by paying attention to yourself.

How can I be more strategic and less reactive?

"Being strategic" sounds like a skill, but it's really about creating space to think. The challenge is that our work cultures often reward reactivity and mistake busyness for productivity.

We'd start by exploring what pulls you into reactive mode. What are you saying yes to and why? What would it cost you to pause? What are you afraid might happen if you slow down?

Then we'd look at how you process information and make decisions. Some people need to think out loud, others need silence. Some need data, others need to feel it. Your path to strategic thinking will be shaped by how your mind actually works, not by following someone else's system.

Why do I keep falling into the same patterns at work?

Patterns repeat because they're serving some purpose, even when they're not working. The key is understanding what that purpose is for you.

We'd explore what these patterns look like and what triggers them. What are you trying to protect or achieve? What are you afraid of? Often patterns are old solutions to old problems that we've carried forward without realizing it.

The work isn't about forcing yourself to change - it's about understanding yourself well enough that change becomes possible. When you see the pattern clearly, you can choose something different.

How do I set better boundaries without seeming uncommitted?

This question reveals a belief that boundaries and commitment are in conflict. But actually, sustainable commitment requires boundaries.

We'd explore what boundaries mean to you and why you fear they'll be misinterpreted. What are you actually trying to protect? What do you need that you're not getting? How could you communicate your boundaries in a way that actually demonstrates your commitment?

Often people discover that their fear of "seeming uncommitted" is actually about something else - seeking approval, proving their worth, or old messages about what it means to be valuable at work.

Can I change my leadership style, or am I stuck with my personality?

Your personality isn't a prison - it's a starting point. You don't need to become someone else, but you can absolutely expand your range and develop new capabilities.

We'd explore what aspects of your current style are authentically you and which are just habits or defenses. What feels essential to who you are, and what's actually flexible? Where do you have room to grow?

The goal isn't to adopt someone else's style wholesale. It's to become more fully yourself while developing the skills to communicate and lead in ways that work for you and the people around you.

How do I give myself permission to lead differently than my boss does?

This is really about authority and autonomy. Somewhere along the way, you absorbed the message that there's one right way to do this, and it's your boss's way.

We'd explore where that belief comes from and whether it's actually true. What would happen if you led differently? What's the actual risk versus the imagined risk? What kind of leader do your people need, and does that match what your boss models?

You get to define your own leadership within your values and your context. That's not rebellion - it's maturity. Finding your way to claim that authority is part of the work we'd do together.

What do I do when my values don't align with company culture?

This is one of the harder challenges because there's no easy answer. Sometimes the misalignment is workable, and sometimes it's not.

We'd explore what specifically doesn't align and why it matters to you. How much flexibility do you have within your role? Where can you create pockets of different culture for your team? At what point does staying become too costly?

I can't tell you whether to stay or go - that's your decision. But I can help you get clear on what you're facing, what your options are, and what you need to make a choice you can live with.

Will you just tell me what to do?

I understand why you'd want that - it would be faster and less uncomfortable. But the truth is, I can't tell you what to do because I'm not you. I don't live in your context, I don't have your relationships, and I don't know what feels authentic to you.

What I can do is help you explore your situation from different angles, ask questions you might not ask yourself, and create space for you to discover your own answers. Those answers will be more durable and more effective than anything I could prescribe because they'll be truly yours.

My role is to be a thinking partner, not an instruction manual.

What if I don't know what I want to work on?

That's completely normal and actually a great place to start. Not knowing is honest.

We'd begin with discovery sessions where we explore what's happening in your work and leadership right now. What's frustrating you? What's working? What keeps you up at night? What do you wish were different?

Through that exploration, themes usually emerge. Sometimes people discover they knew what they wanted to work on all along but were hesitant to name it. Other times, we uncover something unexpected. Either way, clarity comes from the process, not before it.

How honest should I be with you about my struggles?

Completely honest. This work only works if we're dealing with what's really happening, not a sanitized version of it. To be clear I am not a licensed therapist and I’m here to help folks in the context of professional environments. I strongly believe in therapy as a tool to improve ourselves and support you finding someone that you can work with in that capacity.

I'm not here to judge you or report back to anyone. I'm here to help you see yourself clearly so you can move forward. That requires honesty about what's hard, what you're avoiding, what you're afraid of, and what you really want.

The more real you can be, the more useful our work together will be.

What if I try something you suggest and it doesn't work?

First, I want to be clear: I'm not here to give you suggestions to try. That's not how I work. We're exploring together, and any ideas about what to try will come from you, not from me.

But when you do try something new and it doesn't work the way you hoped, that's actually valuable information. We'd explore what happened, what you learned, and what that tells us about what to try next.

This work isn't about getting it right on the first try. It's about building your capacity to experiment, reflect, and adjust. "Failure" is just feedback.

Can I afford coaching at this stage in my career?

That's a question only you can answer, and it depends on your financial situation and what you value.

What I can tell you is that the investment in yourself at this stage often has the biggest return because you're establishing patterns and skills that will serve you for the rest of your career. The earlier you develop self-awareness and your own leadership approach, the more time you have to benefit from it.

That said, it has to make sense for your life right now. We can talk about what's realistic and whether there are ways to make it work, or whether it's better to revisit coaching when you're in a different financial position.

How do I explain coaching to my boss or justify the investment?

If you're asking your organization to pay, we'd want to frame it in terms they care about: your effectiveness, your team's performance, your retention and growth.

You might say something like: "I'm at a transition point where I'm taking on more complex leadership responsibilities. I want to be as effective as possible, and I'd like to invest in coaching to help me develop my skills and approach. This would help me [specific outcomes relevant to your role and the organization]."

If they're open, we can also do a three-way conversation at the beginning to align on goals, though your coaching conversations themselves would remain confidential.

What if my company won't pay for it?

Then you get to decide whether you want to invest in yourself. Many of my clients pay for their own coaching because they see the value in having a space that's completely theirs, with no organizational agenda or reporting requirements.

Self-funded coaching often gives people more freedom to explore questions they might not feel comfortable raising if their company is paying. It's a trade-off: financial investment versus complete autonomy.

Either way works. It just depends on what makes sense for your situation.

Core Principles to Communicate

Regardless of the specific question, here are themes I'd want to weave throughout:

There is no one right way to lead. We tend to fixate on the charismatic leader archetype, but that's just one style. There are as many valid approaches to leadership as there are types of people. Your work is finding the one that's authentic to you.

Communication is the foundation. Almost every leadership challenge is, at its core, a communication challenge. The more clearly you can communicate - with yourself and others - the more effective you'll be.

You already have what you need. My role isn't to fix you or teach you from scratch. It's to help you access your own wisdom, clarity, and capability. You're more resourceful than you probably give yourself credit for.

This is a process, not a program. Leadership development doesn't happen in a straight line. We'll have discovery sessions, we'll identify what needs exploring, we'll practice integrating new skills, and we'll create feedback loops. It's iterative and customized to how you process and grow.

The discomfort is part of it. Growth requires getting uncomfortable. If you're feeling uncertain or exposed or awkward, that probably means we're working on something important. The goal isn't to eliminate discomfort - it's to develop your relationship with it.