The concept of a coach used to be reserved for athletes. Now you can hire a coach to help you with everything from weight loss or parenting to public speaking and career transitions. Even if you whittle it down to business coaches, you could still choose among mindset coaches, sales coaches, or leadership coaches.

If there’s something you want or need to improve, there’s a coach that will help you do it.

So with all these coaches running around, how do you know what’s a worthwhile investment of your time and money?

I can’t speak to the coaching industry as a whole. As you can see, it expands well beyond the scope of a single article. Definitely beyond my reach as a business and leadership coach.

And that’s what I can talk about — what makes a successful leadership coaching relationship.

How do you choose a coach?

The goal of a leadership or business coaching relationship is to help you build competence and gain confidence — with the main focus being on your effectiveness within your organization.

So you need a coach that has the experience and the commitment to guide you through that process. Here are a few things to consider:

Does the coach have enough experience coaching to provide guidance?
Does the coach have experience working with organizations that are your size?
Has the coach been in the trenches with a business of their own?
Can the coach be available to you as much or as long as you need them?
Do you feel confident that the coach will provide a return on the investment?
Have you had a consultation with the coach?
Do the coach’s values align with yours?

You can read more about the details of choosing a coach in our guide The Difference Between Coaches, Mentors, Advisors, and Consultants.

How does the coaching process work?

Every coach has their own process, and the exact method with each client can vary. At Trajectify, we approach our coaching relationships by starting with the gaps. What’s missing that a person or an organization needs in order to meet their desired outcomes?

Our primary goal is to fill the space between where a client is and where they want to be.

First, we determine how dire the situation is. How big is that gap? How aggressive do they (and we) need to be?

The answer determines the intensity, the cadence, and the length of the coaching relationship.

Sometimes we meet with someone twice a month for an hour. Sometimes we’re meeting multiple times a week. There are cases where we work with only the leader, cases where we work with the leader and team, both separately and together, and cases where we work with the team but not the leader.

Second, we learn everything about the organization — their numbers, their organizational charts, their key processes. We love to start with an organizational assessment, though they’re not feasible for every organization.

No matter the size or scope of the engagement, we’re looking for opportunities to improve the organization as a whole.

Third, we meet with the client (leader or team members or both) and come up with goals — short-term and long-term, business and personal.

Why both business and personal goals?

If you’re a business owner or running your own business, you need your company to align with your personal reasons for building that business. Otherwise, you’re going to run into a lot of conflict. And we get called in to address those conflicts — from not having enough money in the bank to having a debilitating work-life balance.

We always create SMART (Specific, Measurable, Achievable, Realistic, and Timely) goals, along with a detailed plan to meet them.

Fourth, we meet with the client and hold them accountable for what they said they were going to do.

Throughout the process, we try not to be prescriptive. 90% of the time, we’re asking questions and helping our clients think through and solve their own problems. Then we’re there to make sure they do what they said they’d do to meet their goals.

How can you measure the effectiveness of a coaching relationship?

The bottom line matters for any organization. Every investment has to have a positive return. Business owners don't come to us just because they think coaching is a good idea (though it is). They often come to us because they’re aware of a gap. They’re not making their sales numbers. Their teams aren’t getting projects completed on time. They don’t know what to do next.

Even if the issue isn’t metric-oriented, there’s a cost.

They’re having trouble retaining people. There’s too much conflict. They’re having trouble making decisions or taking risks. They don’t know what step to take next.

There are costs to all of these. Sometimes the coaching process helps identify the mechanisms for measuring these costs. Sometimes they’re already clear.

We have a client who hasn’t seen their coach in a month because they are too busy, but they’re also not sure if they should hire someone. So they stay in the trenches and do all of the work, and we know where that leads. To burnout. To disappointing a client. To screaming for help because things have gotten too crazy.

Or they could work with their coach, step back a bit to get an outside-in and unemotional perspective, and see what the next step might be. Then start to make decisions and act on them.

Right now they’re stuck. Many entrepreneurs and business owners get that way.

Our process is about helping get unstuck.

Sometimes our clients simply need some perspective and a little confidence.

For instance, I worked with someone who reported to the CEO but couldn’t get any time on his calendar. I asked whether they’d ever sent the CEO a calendar invite. “I can do that?” they asked.

We tried it, and the client ended up with a standing bi-weekly meeting with their CEO.

Other times, they’re learning how to be a coach themselves — to their team members, or even to their bosses.

This year we worked with several mid-level managers at one company, each who had some gaps that needed to be filled. Almost all of them had a ceiling that was immovable unless we could work with the rest of the organization. That wasn’t part of our contract, so we had to coach each of those individuals about how to manage up — so that they could, in a sense, coach their bosses. We do that a lot. (Three of the four got promotions.)

Every step of the process is focused on helping the individual and the organization meet their goals.

What does a bad coaching relationship look like?

The biggest way we see coaching go wrong is when it’s used for punitive purposes.

Yes, coaching is a great way to help someone perform better. The problem in a punitive situation is that it’s almost always done as a last resort. The manager didn’t start out by offering continuous feedback, by confronting problems early on in a caring and constructive way. The first level of coaching should always be done by an effective manager.

Often when we’re called in for a remediation-level coaching, there have already been tons of missed opportunities. At that point, we really need to be coaching the manager as well. If something isn’t working between a manager and a team member, the issue is never just the team member’s. They’re in a relationship together, and they’re both responsible for its success.

The other big problem I see with some coaching relationships is a confusion about scope. Business coaches aren’t psychotherapists. They don’t have that kind of training, and it’s not effective (or ethical) for them to engage in that type of work.

There are coaches who really want to address the underlying causes of personal issues as part of the coaching relationship, and that’s just not how I work. I’m not a therapist. I focus on bridging the gap, growing your confidence or your competence from where you are right now, regardless of what came before.

Final thoughts

Many years ago, my family decided to schedule a guided rappelling tour while we were on vacation in West Virginia.

There was only one problem: I’m afraid of heights. Weak in the knees when I stand by the window of a tall building afraid of heights. (And to think that I grew up in an 18th floor apartment in NYC.)

I didn’t want to spoil the fun. I had a plan. My kids would go first, and seeing them down at the bottom would compel me to get myself down there too — as their father.

It didn’t work. So much for parental instincts.

My children looked up at me from 150 feet down, and I could not move from the edge of that cliff. My body would not do it. The guide gets me into the gear and explains to me how it works. I’m a science guy. It makes sense. So I back up to the edge of the cliff, where I’m supposed to bend my knees, sit back into the harness, and push off the side of the cliff.

The guide explained the physics of rappelling to me. I understood it. And my body still wouldn’t cooperate.

The guide tried different methods of coaching to get me to approach the cliff, release my weight into the harness, and allow the rope to guide me down. What finally worked were micro steps — breaking it down into the tiniest pieces so that my brain didn’t get overwhelmed with where I might be going next. Move your left foot back half a step. Bend your right knee.

When I finally made it to the bottom, the guide told me he had four techniques to get anyone down the mountain, and that he’d never failed.

The techniques aren’t important — what sticks with me now is his sense of responsibility. I’d set the outcome I wanted to achieve: rappel down this mountain and meet my children at the bottom. His job was to figure out how to help me achieve it.

This is perhaps a long-winded way to say that a coach can be critical in helping you meet your goals. Without that guide, I’d probably still be atop the mountain looking at the edge of that cliff. And the right coach can make a huge difference. And if he had only had three techniques instead of four...who knows where I’d be.

Take the time to choose a coach that you have confidence in and who’s committed to your success. A good business coaching relationship can be the difference between success and failure.