What a Six-Month Executive Coaching Engagement Actually Looks Like

A six-month executive coaching engagement has five parts: a three-way alignment meeting, an assessment, a 360 built from interviews with five colleagues, a written leadership development plan, and twelve 50-minute coaching sessions. Here's what each one involves, week by week.

Most firms describe this process in the abstract. We publish the specification, so this piece walks through a real engagement: who's in the room at each stage, how long it takes, what comes out of it, and where it goes wrong.

The specification itself lives on our executive coaching page. This is the version with the detail a buyer and a coachee actually need.

Step one: the three-way alignment

The three-way alignment is a meeting between the coach, the leader being coached and that leader's own boss, held at the start, the mid-point and the close. It runs about an hour and it produces the agreed goals for the engagement.

Three people, one conversation. The leader says what they want to work on. The boss says what they'd notice if it worked. The coach's job is to get those two answers into the same sentence before anyone spends money.

The output is a short written set of goals all three have agreed to. Not a competency list and not a performance improvement plan. Two or three specific things that should be different by month six, described in behavior rather than in adjectives.

This meeting also sets the confidentiality boundary out loud, with all three people present. That matters more than it sounds, and there's a section on it below.

The mid-point alignment checks progress against those same goals. The closing alignment reports what changed and what the leader is continuing on their own. Same three people each time.

Step two: the assessment

The assessment happens in the first month and takes the leader 15 to 30 minutes to complete. The instrument gets chosen to fit the leader and the goal rather than applied by default, and the debrief with the coach takes about 90 minutes.

Six instruments cover most situations, and they read genuinely different things:

• Hogan reads derailment risk: the behaviors that show up under strain and damage a leader's reputation. Eleven scales, 15 to 20 minutes, and the one to choose when a strong leader keeps hitting the same wall.
• Birkman reads what a leader needs to stay effective and how their behavior shifts under stress. Useful when the gap is between how someone means to come across and how they land.
• Leadership Circle Profile is itself a 360, structured around creative competencies on one side and reactive tendencies on the other, across 29 dimensions. It's the choice when the question is how a leader's mindset shapes their impact.
• Gallup CliftonStrengths reads natural talent patterns across 34 themes. Best in developmental engagements rather than corrective ones.
• DiSC reads behavioral style across four preferences. Fast, accessible, and the right choice when the work is about adapting communication to different people.
• EQ assessments read emotional intelligence across five composites and fifteen subscales. The choice when the goal involves self-regulation, empathy or how a leader handles pressure.

The debrief is the part that matters. A report emailed to a leader produces a mildly interesting afternoon. A report walked through by a coach who then asks what the leader recognizes in it produces the first real session of the engagement.

The leader owns the assessment results. They aren't shared with the organization.

Step three: the 360

The 360 is built from confidential interviews the coach conducts with five of the leader's colleagues: typically their boss, a couple of peers and a couple of direct reports. Each interview runs 30 to 45 minutes, and the whole step takes two to three weeks.

Interviews produce different material than survey instruments. A survey returns a number for "communicates effectively." An interview returns the story of the meeting in April where three people left unclear about what had been decided, which is something a leader can actually act on.

The coach delivers the findings as a written summary, organized by theme, with no comment attributed to any individual. The leader reads it with the coach in the room, because the first read of a 360 is rarely a calm one.

The organization doesn't receive the 360. Neither does the leader's boss, even though the boss was one of the five interviewed.

That last rule is what makes the interviews worth doing. Colleagues speak candidly because they know the material goes to the leader as a theme rather than to the organization as a quote.

Step four: the leadership development plan

The leadership development plan is a written document built from the assessment and the 360, drafted by the leader with the coach, and shared with the leader's boss at the mid-point. It's usually two to four pages.

The plan names two or three areas of focus, the specific behaviors that go with each one, and how progress gets recognized. It's written in the leader's own language, because a plan written in the coach's language gets read once.

Sharing it with the boss at the mid-point is deliberate. The boss sees what the leader is working on and can support it. They don't see the 360 or the assessment that produced it.

The plan gets revisited in the second half of the engagement. Plans that survive month six unchanged usually weren't specific enough to begin with.

Step five: the twelve coaching sessions

Twelve sessions of 50 minutes each, spread across six months. That's roughly every other week, and the spacing is the point.

Coaching works in the gap between sessions. A leader commits to a specific conversation, has it or avoids it, and brings back what happened. Sessions every week don't leave enough room for the leader to actually do anything, and sessions once a month lose the thread.

Sessions are led by the leader's agenda inside the agreed goals. A typical one opens with what happened since last time, works on a live situation the leader is facing, and closes with something specific they'll do before the next one.

Twelve sessions is 10 hours of coaching time. The rest of the program, the assessment, the five 360 interviews, the plan and three alignment meetings, sits outside that number and takes the coach considerably longer than the sessions do.

Confidentiality: what the sponsor sees and what they don't

The sponsor sees the goals, progress against those goals, and whether the leader is engaged. The sponsor never sees session content, assessment results or the 360.

That's the line, and it holds in both directions. A coach who reports on sessions has a coachee who stops saying anything real. A coach who reports nothing at all leaves the organization funding something it can't evaluate, which is why the three-way alignment structure exists.

In practice it works like this. If a leader spends a session working through whether to leave the company, the sponsor doesn't hear about it. If the leader stops showing up to sessions, the sponsor does, because attendance is a term of the engagement rather than content.

Three specific questions come up often enough to answer directly.

Can the coach be asked to inform a promotion decision? No. Coaching stops being coaching the moment it feeds an evaluation, and any firm that agrees to this arrangement is selling you something else.

What if the coach hears about something serious? The engagement agreement should name the narrow set of circumstances where a coach has to break confidence, and both the leader and the sponsor should see that language before signing.

Who owns the assessment data? The leader. It goes with them.

Get all of this in writing at the start. A firm that handles the question casually in the sales conversation will handle it casually later.

What the sponsor is expected to do

The sponsor's job is bigger than paying for it, and buyers underestimate this consistently.

Research from the Center for Creative Leadership, covering 347 leaders and more than 3,000 raters, found that 68 percent of leaders whose supervisors supported the coaching made substantial progress on their goals, against 42 percent of those whose supervisors didn't. That's a 26-point difference produced by the boss rather than the coach.

Concretely, the sponsor commits to four things. Show up to all three alignment meetings. Say plainly what would be different if it worked, at the start, rather than "better leadership." Notice and acknowledge changed behavior when it appears, because a leader who changes and is told nothing concludes it didn't matter. And protect the time, since a leader who cancels four sessions for operational reasons has been told what the organization actually values.

What makes an engagement fail

Three failure modes account for most of it, and all three are visible before the first session.

The coachee was sent rather than chose. A leader handed a coach as a consequence will be polite, attend everything and change nothing. This is the most common failure and the most avoidable one. The fix is a genuine choice, including the choice to decline, and a real conversation about why the organization is offering coaching before anyone enrolls.

The sponsor disengages. The boss who set the goals gets pulled onto something urgent, skips the mid-point alignment, and by month six can't say whether anything changed. The engagement then gets judged on a feeling.

The goals were never really agreed. Everyone nodded at "improve executive presence" and nobody defined it. Six months later the leader thinks they did the work, the boss thinks nothing happened, and both are right by their own definition.

There's a fourth, less common and more damaging: an organization uses the assessment or the 360 as an evaluation input. It usually happens once, informally, and the word travels through the leadership population faster than any communication plan can catch it.

After that, nobody in the building says anything real to a coach again.

If you're considering an engagement

The specification above is what we run. Our nine coaches are all ICF certified and all held corporate executive roles before they got certified, which is why the sessions tend to skip the part where a leader has to explain what a quarterly business review is.

Six of the nine, including the founder, trained through the Hudson Institute of Coaching. That shared training is why the five steps above run the same way whichever coach you're matched with.

If you want to talk about a specific leader and whether this is the right fit, get in touch. If you're still deciding between providers, we wrote a buyer's guide to choosing a coaching firm that compares the four categories without naming anyone.