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How Structured Should Your Career Coaching Sessions Be?

Updated: Feb 4



“The client sets the agenda” is a common mantra of life coaches. And with good reason. Life coaches are generalists who handle a wide range of issues, and it’s reasonable for the client to decide what should be top of mind at a given time. Putting the burden of responsibility on the client for the “scope of work” also serves the stealth function of teaching folks to advocate for themselves and discern what’s really on their minds.

But we’re not life coaches.


Career coaches are different, and to be honest, people don’t hire us hoping for an open-ended chat. We’re tactical. We have an objective: identifying and landing the right job for the client—and ensuring they have the tools to thrive when they get there. Flexibility is definitely part of the job, and different clients have different needs—but generally, for career coaches, structure is a good thing.


I have a very set agenda of what I would like to cover and get done each week for the first two months. Clients love having a plan, and structure. Most career coaching clients benefit tactically and emotionally when they have checklists and action items and a plan.

Of course, flexibility needs to be built in. There are “hijackings” where a client suddenly needs to triage a particular situation. For example, one of my clients, a VP of Marketing, was slated to be one of the top picks to be promoted to CMO. But right before one of our sessions, she heard that her rival was promoted to SVP of Marketing, pretty much setting the rival up to be heir apparent. Naturally, my agenda went out the window and we talked about this specific situation. Being rigid would have let her down—she needed to regroup and that meant so did I.


What are the most important things to cover in your first 2 months with your client?

  1. We help them land on their ideal job—the one that gives them the chance to do something they love, and are good at, and will pay them what they deserve to be paid.

  2. We redesign their dossier for them—primarily their resume, their cover letter template, and their LinkedIn profile. We do this for them because most people are horrible at writing about themselves and don't integrate marketing into their dossier.

  3. We develop a go to market strategy that helps them get in front of the right people in the job search process. The GTM strategy is based on three major channels: job postings, personal network, and executive third party recruiters.

  4. We help them shine during conversations by teaching them executive presence skills, including “gotchas” to avoid and manage during the interview process.

Meeting those objectives within your first two months with a client is nearly always attainable, and it’s very reassuring for clients to feel like there’s a cogent plan that will get them where they want to be. Being unemployed, underemployed, or in a job that’s causing distress is psychologically taxing. Your clients are looking for more than emotional support. They want to close the gap between where they are and where they want to be, and usually, they need it to happen fast.


Most of your clients will come to you under considerable stress. They’re not looking for a therapist; they’re looking for a problem-solver. That’s not to say you won’t address therapist-adjacent stuff about “purpose” and “feelings” and personality style and fears and anxieties—you often will. In fact, sometimes that stuff is a skeleton key to why they’ve been struggling to land that job (talented client who tends to have interpersonal conflicts with managers; Impostor Syndrome person who accepts less than they’re worth and then festers about it; client returning to the workforce after a long absence who is petrified—these things do require your inner therapist to make an appearance sometimes).


But presenting them with a plan and showing them how you’re both going to follow it is important. For a career coach, structure is definitely a friend.


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