What 60 Days of Coaching Looks Like — From the Inside

Most people don't know what executive coaching entails until they're already in it. Here's the honest week-by-week breakdown.

I've had some version of the same conversation more times than I can count.

Someone reaches out — a senior director, a VP, or an emerging individual contributor who's been quietly following my content for a while. They're thoughtful and accomplished, clearly someone who takes their development seriously. At some point in the conversation, usually after we've established that there's something real going on that coaching might help with, they ask the question they've been circling:

"But what does it actually involve?"

Not the brochure version. The real one. What happens in the room. What a session feels like. What changes, how fast, and what it costs in terms of discomfort before it starts feeling like something other than discomfort.

It's a fair question. Coaching is one of those things that's easy to recommend in the abstract and hard to describe concretely — which means a lot of people who would genuinely benefit from it talk themselves out of it because they can't picture what they're committing to.

So this is my attempt to answer that question honestly, with as much specificity as I can offer without violating the confidentiality that makes the work possible in the first place.

Here's what 60 days of coaching with me looks like from the inside.

Before Week One: The Conversation That Determines Everything

We start before we start.

The first conversation — which is always free and meant as a conversation rather than a sales call — is not about convincing anyone of anything. It's about figuring out whether this is the right fit. Not every coaching relationship is. Not everyone is ready for this kind of work at a particular moment in their career, and I'd rather know that at the beginning than three sessions in.

What I'm listening for in that first conversation is specificity. Not "I want to be a better leader" — that's an aspiration, and it's a good one, but it doesn't tell me enough. What I'm listening for is something more like: "I keep having the same conversation with my senior stakeholders, and it never lands the way I intend." Or: "I've been passed over twice, and I understand the feedback, but I don't know how to act on it." Or: "My team delivers, but I don't think they trust me, and I'm not sure why."

Specificity means the person has been paying attention. It means there's something real beneath the surface that we can work with. And it usually means they're ready, even if they're nervous about what readiness involves.

Week One: Truth Before Goals

Most people come to coaching expecting to spend the first session setting goals. We don't.

Not because goals don't matter — they do, and we'll get to them. But in my experience, the goals people articulate at the start of a coaching relationship are almost always slightly off. They're the goals that feel safe to name, the goals their organization has told them they should have, or the goals that address the symptom rather than the underlying issue.

So, week one is about something different. It's about getting honest about what's actually true right now — not the performance-review version of true, not the version you'd tell in a job interview, but the version you'd tell a trusted colleague at the end of a long day, when you're not managing how you sound.

What's working? What isn't? Where do you feel most like yourself at work, and where do you feel like you're performing a version of yourself that's slightly off? What are the things you keep meaning to address and keep finding reasons not to?

This part takes longer than people expect. And it often surfaces something that surprises them — not a revelation, exactly, more like a recognition. Something they already knew but hadn't quite said out loud yet.

That recognition is usually where we start.

Weeks Two and Three: Naming the Pattern

Here's something I've observed across almost every leader I've worked with, regardless of industry, level, or organizational context:

Underneath whatever specific challenge brought them to coaching, there is almost always a pattern. A recurring dynamic that shows up across contexts, teams, and stages of their career. The way they handle conflict — or avoid it. The way they seek certainty before acting, or act before they've thought it through. The way they shrink in rooms with more power or overextend when they feel their authority is being questioned.

These patterns aren't flaws. They were almost always adaptive at some point — something that worked in a prior context or under earlier pressures. But they've run so long and so automatically that the person can no longer see them clearly. They just seem like the way things are. Weeks two and three are about making the pattern visible.

This is the most uncomfortable part of coaching for most people, and I want to be honest about that rather than softening it. Being shown a pattern you've been living in without seeing is disorienting in the way that any reorientation is disorienting — not painful, exactly, but it takes a moment to get your bearings.

In this phase, I try to hold the mirror steadily and make the observation without turning it into a verdict. The pattern isn't who you are. It's what you've been doing. And what you've been doing can change.

Weeks Four Through Six: Where Insight Becomes Behavior

This is the phase most people underestimate before they experience it — and the one they talk about most afterward.

Because coaching isn't therapy, consulting, or mentorship. It's a practice. That means that once we've named what's actually happening and identified the pattern underneath it, the work is to change behavior in the real world, in real time, in the situations that are actually happening this week.

Not in a hypothetical. Not in a role play. In the conversation with your CFO that's scheduled for Thursday. In the 1-on-1 with the direct report who's been disengaged for three months. In the leadership team meeting where you've been staying quiet about something you know needs to be said.

A coaching session before that meeting looks different from a coaching session about leadership in the abstract. We talk about what's at stake, what you're afraid of, what you've tried before and why it didn't land, and what it would look like to show up in that moment as the leader you're working toward being.

And then a session after the meeting is equally important — not to evaluate how you did, but to understand what you actually experienced in that moment versus what you expected. What shifted. What was harder than you thought it would be. What surprised you. What you'd do differently. This is where the real learning happens. Not in the insights, but in doing things differently and debriefing what that felt like.

Weeks Seven and Eight: Consolidation

By the time we reach the final two weeks of an initial engagement, something has usually shifted. I want to be careful how I describe this, because I've read enough coaching testimonials to know that this is where they start to sound like advertisements.

So let me try to be specific about what I mean by "shifted."

It's rarely dramatic. It's usually something quieter — a moment when someone realizes they handled something differently than they would have eight weeks ago. They had the conversation they'd been avoiding. They stayed in the room instead of shutting down. They asked for what they needed from their team instead of resenting having to ask.

These moments don't always feel like victories when they happen. Sometimes they just feel like a slightly less uncomfortable version of something that used to be very uncomfortable. But they're durable in a way insight alone never is.

Weeks seven and eight focus on naming what changed — specifically enough for the person to recognize, articulate, and sustain it without me in the room. We're not building dependency. We're building a leader with greater access to their own thinking, greater clarity about their own patterns, and greater confidence in their ability to navigate the hard moments that will inevitably keep coming.

The coaching engagement ends, but the work continues.

What It Actually Costs

Not in money — I'm happy to discuss that in a first conversation. The investment varies depending on what kind of engagement makes sense for where someone is.I mean what it costs in terms of honesty, time, and willingness to be uncertain about yourself.

Coaching requires a willingness to not have the answer. To sit with a question that doesn't have a clean resolution. To look at a pattern you've been living in and not immediately try to fix it before you've truly understood it.

For high performers — which is most of the people I work with — this is the hardest part. High performers are used to being the person who figures it out. The person who doesn't need to be told twice. The person who reads the book, implements the framework, and checks the box.

Coaching isn't a box to check. It's a relationship with your own development that deepens over time. And that requires something different from performance. It requires presence.

If you can bring that — most people can once they decide to — the 60 days will give you more than any course, book, or seminar I know of.

Not because I'm extraordinary. Because you already have what you need. Coaching simply helps you access it.

If You've Been Wondering Whether This Is for You

The fact that you've read this far is information.

Most people who are genuinely not interested in coaching don't read a 1,500-word article about what it involves. They skim the first paragraph and move on.

If you're still here, something resonated. Maybe it's the pattern piece. Maybe it's the recognition that you've been performing certainty you don't feel. Maybe it's the sense that something is working in your career, but something isn't quite right beneath the surface, and you haven't found the right language for the second thing yet.

That's exactly the conversation I want to have with you.

Not to sell you anything. To find out what's actually going on and whether this is the right fit for where you are right now.

The first conversation is always free. No pressure. No pitch. Just an honest conversation about where you are and what you're trying to build.

Antoine E. Burrell, Sr., is a Senior Engineering Manager at Cloudera and the founder of Alpha Bravo Professional Coaching, a Co-Active coaching practice for technical and executive leaders across IT, finance, healthcare, defense, and consulting.

Ready to have that first conversation? Visit alphabravocoaching.com or connect on LinkedIn.