Career Coaching: Is It Right For You?

If you’re reading this article, there’s a pretty good chance that you’re contemplating a job or career change in the near future. And you’ve probably been wrestling with the best tips and ways to make that pivot happen.

A lot of people work with a dedicated coach, counselor or advisor to make the change a reality. But signing up for this help is potentially a big decision.

So how do you know if working with someone one-on-one is really a good investment of your time, energy and money?

Here are ten things to consider when deciding if working with someone is a good idea for you:

1. Your Path is Fuzzy.

Some people who are looking to pivot know exactly what they’re looking for, (aren’t we jealous…), but most people don’t. If you’re not sure what kind of job to look for, or what kinds of fields to explore, the process of figuring it out might take a while.

Working with someone one-on-one gives you the individualized attention to figure it out, and often times a good coach helps you come to those conclusions on your own, they just guide you through the process.

2. Your Situation Is Complicated.

If you’ve had a number of various jobs in different fields, took time off for something, or are trying to make a significant change in your career how you get from point a to z might not be so clear.

If you feel like general tips and tricks don’t seem to work for you, then this is when a coach becomes invaluable and can be your individual troubleshooter and strategist. And in this case, figuring out your personalized strategy for your resume, interviewing, and job seeking is critical.

3. You Can’t Or Don’t Want To Be Public.

If you have a sensitive situation or really can’t risk others finding out that you’re job seeking, for whatever reason, then working with a coach who maintains your confidentiality is important.

They can help you think through how to structure your job search and how to navigate the details when you have to troubleshoot your boss finding out, or your staff hearing that you’re looking to leave.

Even if you’re not worried about your friends or colleagues finding out that you’re looking to transition, not all of us love being public about the process and how it’s going. Another good reason to have someone on speed dial who will keep everything with you on the DL.

4. You’ve Been Struggling or Searching For a While.

If it’s been more than six months that you’ve been overwhelmed, unmotivated or uninspired about your next career move, you need a dose of something new. It’s time to shake it up with a new approach.

A new method, different questions to ask yourself, and fresh ways of thinking through your situation might be just what the doctor ordered. And often after six months or more, it’s helpful to get an outside perspective.

5. You Need Accountability.

Yea… you know who you are. You totally had a plan to update your resume on Saturday afternoon but following through on it was harder than you thought it would be. Especially when you don’t have someone looking over your shoulder to report back to about how your search is going. That is a-ok! And that’s why you work with someone who is responsible for checking in on you, helping you prioritize your to-do list, and acting as personal career trainer, pushing you along.

6. Talking About Yourself in Public Gives You Hives.

A huge part of securing your dream job is making a public case for it – either in front of your network, or at the very least, the person who’s interviewing you. This can give anyone anxiety.

If you’d rather practice and refine your pitch in front of one person, rather than a whole group of people, private coaching is for you. If you’re someone who gets ideas and gains confidence surrounded by a lot of other people, then a group program might be better for you!

7. You’ve Tapped Out Your Friends.

We all reach out to past bosses, mentors, and our friends when we’re in transition. In fact, your friend network might be the easiest for you to look to for advice or contacts in your job search.

But if you feel like you’ve gone to that friend who’s always happy to look at your resume one too many times then it might be time to solicit support from a coach. Most are also happy to make a few connections for you as well, which opens you up to a larger network that doesn’t make you feel like you’ve used up your quota of asks.

8. You’re a Busy Person.

If your schedule is packed or always changing, committing to a group program can be tricky. Working one-on-one with a coach allows you to schedule your own sessions at times that work for you. If you want to do sessions every week or alternatively every few weeks, most coaches are flexible.

And most coaches usually let you reschedule a session if something comes up as long as you give enough advanced warning. If you need flexibility, this is a good route for you to go.

9. You Think You Might Need Support More Than Once.

One of the great things about working with someone one-on-one is that you can go back to them and pick up where you left off when it’s time for your next pivot.

When I work with someone, we use a shared Google folder with all our session documents so that when we need to pick back up with coaching it’s all there in one place and there are notes to jog our memories on what we’ve discussed before. Any good coach will have something like this so that you can go back to them in 5 or 10 years when you’re in a transition phase again.

10. You Highly Value Your Career.

Many people view their day job as just that – a job you do from 9am to 5pm that isn’t particularly meaningful but pays the bills. If you want your job to be as energizing and meaningful as possible for you, that means really knowing who you are, what your strengths are, and where you can make the most impact in the world.

Coaching helps you go deeper to understand all of these things with someone who is your cheerleader and is committed to supporting you and seeing you succeed in something you really enjoy.


If you’re considering working with a coach, do your research on what various people offer - you’d do it for any other kind of consultant or professional that you’d hire to help you with anything!

Some coaches charge a flat rate per session, and many offer packages of a certain number of sessions that give you a slight discount. And some, like myself, offer a specific curriculum or outline of services that they specialize in.   

Once you’ve done your research, you’ll probably want to have a conversation to see if it’s the right fit. Approach, personality, style, chemistry - all these are important aspects of a good client-coach relationship.

Many coaches, like myself, offer a free short session to see if working together would be the right fit for you and them. And if it’s not a free session, they’ll often offer the option of putting the cost of the exploratory session towards your first official session.

Whether or not you decide to work with someone one-on-one, one thing is a must: don’t settle with your current career situation if it isn’t working for you or making you happy.