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Hiring a Retirement Coach? Here’s What to Look For

Hire the right retirement coach

Credit: iStock

By Joe Casey


Who needs a retirement coach?  There will be over 3.6 million people in the US turning 65 each year for the next two decades. [1]  And with many pursuing early retirement, there are more people than ever before navigating the transition to retirement.  And there’s a growing cadre of retirement coaches ready to help. But it’s important to hire the right retirement coach for you.


What’s Driving the Growth in Retirement Coaching?

Retirement is a major life transition with a significant emotional component. There’s a growing awareness that retirement is about much more than money. It’s easy to fall into the trap of becoming narrowly focused on saving for retirement while ignoring that you also need to prepare for how to retire well.

Retirement today lasts much longer than in previous generations and a 20 to 30-year retirement is not uncommon. That span requires a smart plan on how you’ll invest your time. It’s becoming seen as a new phase of life offering opportunities for re-invention, rejuvenation, learning, and contribution. In a recent survey, 65% of women and 62% of men reported that they “anticipate retirement as a time to rediscover themselves.” [2]


Retirement is Customized Today – and Often Still Includes Work

Is there a One Size Fits All approach for retirement? Today there’s no one way to retire – and there’s no standard roadmap. You have to chart your own course, which is a great opportunity, but it comes with challenges.  And while retirement used to mean leaving work behind, today it often includes work in some form. According to a survey by the Employee Benefit Research Institute, 8 of 10 workers expect to work for pay in retirement.[3] It’s often not out of financial necessity but for the rewards offered by meaningful work. Because your retirement is unique, the right retirement coach can be a valuable asset.

Retirement comes with opportunity, change, and uncertainty. There are hurdles to jump over and some may come as surprises. You’ll need to think through how to replace some of the benefits that work provided you beyond your paycheck; such as your identity and purpose; how you structure your time; and how you are socially connected.  A study by Age Wave & Merrill Lynch found that on average retirees took 2.5 years before deciding what to do next. [4] If you hire the right retirement coach, it can help you avoid the drift, gain clarity on your direction – and get you to where you want to go faster.


What Does a Retirement Coach Do?

If you just want to kick back, watch TV, travel and play golf in retirement you won’t need a coach. But, if you want more from life, a retirement coach can help you find and realize your vision of a satisfying life in retirement.

A retirement coach helps you plan for the non-financial aspects of retirement. The primary focus is on how you want to invest your time, which is perhaps your most precious asset of all. A good coach can help you expand your thinking, test new options and help you build a portfolio of meaningful activities. Retirement coaching is about thoughtfully designing your next chapter and successfully navigating the transition from corporate life to your new life.


6 Steps to Hire the Right Retirement Coach 


There are more great retirement coaching options than ever before. With so many choices, how do you find the coach that’s best for you? Before you invest your hard-earned money and your valuable time, do a bit of due diligence:


  1. Do Your Homework. What will success will look like if you work with the right retirement coach? Giving it some thought in advance will help you make the right choice. Use a variation of the question highlighted by Carl Richards.  Picture a friend running into you next year and asking you  “Hey, what did working with that retirement coach do for you?” Jot down your initial ideas about how you think it will have helped you. You can clarify it as you go along, but it gives y0u a good starting point for conversations with prospective coaches.
  2. Write a Short List of Criteria. Make a list of what’s most important for you in choosing a coach. How important are factors like their experience and training? Does the coach need to be in your local area or are you open to working virtually? How important is the cost? You’ll find retirement coaching to be far less expensive than you might think. (Insider Tip: Hiring a local coach you can work with in-person isn’t necessarily more effective than hiring a coach who’s better for you working virtually. Work with the one that’s best for you).
  3. Interview Three Coaches. Select three coach candidates to interview. Let each one know that you’re talking with three options and that you’ll let them know your decision. I recommend including different types of coaches. For example, talk with a mix of male and female coaches. Even if you have a preference, include a mix of coaches who work in-person and virtually.
  4. Ask About Their Coaching Approach and Process. Go first. Ask your questions of the coach. Why? You’ll want to see how good a listener your coach is. It’s critical. Ask each coach to describe their approach and how their process works. (Insider Tip: Ask what their process is based on. The answers will tell you a great deal. Look for substance, not buzzwords.) Inquire about how they were trained, and how many clients they have coached. Ask for an example of a recent successful coaching engagement – and ask about for a story of an unsuccessful one and what they learned from it. These questions will help you gauge their training and experience level.
  5. Watch What They Ask You – and What They Don’t. When you turn it over to the coach, pay attention to their questions. Now it’s your turn to listen. What do they focus on and what does that tell you? Are there key things they didn’t ask about that perhaps they should have?
  6. Request  References. Request three references of previous coaching clients you can reach out to. You’ll learn a lot.



Hiring the right retirement coach can help you design an active, satisfying life in retirement. There are many great options for retirement coaching, but do a little homework, interview multiple coaches and find the one that’s a great fit for you. Make sure the chemistry and location work, but don’t let those factors limit your choices. Be careful and consider only well-trained, experienced coaches with solid references that can help you create the pathway that’s right for you and your specific goals, priorities, and circumstances. It can make all the difference.


Joe Casey is a former senior HR executive who’s transitioned to a second career as a retirement coach at Retirement Wisdom. He holds a Masters in Gerontology from the University of Southern California and works with people to help them discover and design what’s next after their primary career.  He’s the co-host of The Retirement Conversation podcast talking with authors, experts and retirees pursuing interesting Second Acts who share their stories, insights, and lessons learned that can help you in your journey.


[1] (May 30, 2019). How Many People Will Be Retiring in the Years to Come? The Federal Reserve Bank of St. Louis.

[2] (April 23, 2019).  2019 Retirement Confidence Survey. Employee Benefit Research Institute.

[3] (September 10, 2018). The Future of Retirement: Bridging the Gap.  HSBC.

[4] (2014). Work in Retirement: Myths and Motivations. Age Wave/Merrill Lynch.










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