As a retired psychologist and longtime member of XPX Chicago, I’d like to share some thoughts about how to help people successfully transition from work.
We know that advance exit planning – five to ten years out – provides our clients with far more options and greater flexibility than they might otherwise have. My colleague from XPX Charlotte, Tom Bixby, wrote an outstanding and comprehensive whitepaper about this topic. But too many business professionals and advisors don’t raise exit planning until much later. What would you think if your physician waited until you were 60 to discuss how regular exercise could forestall the effects of aging?
It’s reasonable to assume that multiple discussions will be needed to spur people to begin exit planning. If that’s true, we ought to be speaking with current clients and potential prospects about this topic – early and often. Here are six things we tell ourselves that get in our way of doing so, and how to counter them:
- I’m familiar with exit planning, but that’s not my primary professional role.
- It’s too early; it’s hard enough to get people to focus on it 1-3 years out.
- It might make my client uncomfortable.
- I’m not sure how to raise the issue without it seeming forced.
- There isn’t much I can offer so far ahead.
- I’m hesitant to ask clients to tackle something I haven’t fully addressed myself.
I’m familiar with exit planning, but that’s not my primary professional role . . .
There are legitimate arguments to stay in your lane. For example, psychologists have an ethical mandate prohibiting practice outside one’s area of competence. But that doesn’t mean we’re not expected to know about matters beyond our daily work. I wasn’t trained to treat children, so I didn’t, but my profession (and the State licensing board) still expected me to know how to identify and report suspected child abuse.
It’s easy to convince ourselves that because our clients hired us for a specific task, we can ignore tangential but important issues. I think that does people a disservice. I wasn’t a physician, but if a new patient told me they hadn’t had a physical exam in over a decade, you better believe I hounded them to get one. If they announced their intention to start a new business venture, I made it clear that speaking with an attorney and an accountant upfront could help them avoid numerous pitfalls later. When you make a reasonable, defensible recommendation in your client’s best interests (even if it’s outside your bailiwick) you’re doing what any thoughtful professional does: you’re paying attention to the whole person, not just the transaction.
It’s too early; it’s hard enough to get people to focus on it 1-3 years out . . .
It can be hard for some owners to think 5-10 years out, especially those whose future orientation isn’t strong. But remember, all you’re doing is asking them to have a conversation with you about an important topic. If early exit planning sounds like too much of a stretch, you can frame it as “long term strategic planning” and add, “we should make sure you’re setting yourself up in a way that makes sense for the duration of your business rather than leaving things to chance.”
Clients may protest that they’re too busy with pressing problems to focus on the future, but we know that by targeting long term challenges we can resolve current issues, too. For example, a business owner may insist they’re too tied up with employee turnover to think about developing their senior managers. You could say, “long-term, the value of this business is at risk if you’re putting out fires every day. If we upgrade your senior managers now, they can deal with personnel issues while you steer this ship toward a profitable port.”
It might make my client uncomfortable . . .
I suppose that’s possible, but when you consider the range of difficult conversations business owners have likely had throughout the course of their career, I suspect that this wouldn’t even make the top 10.
If you don’t invite them to have this discussion early, you’re colluding with them in avoiding a critical conversation that’s in their best interest. And even if it’s hard for you, that doesn’t mean you shouldn’t do it. Your doctor probably doesn’t enjoy asking sensitive questions that make you uncomfortable, but that’s part of being thorough.
I used to tell my patients, “the right decision doesn’t always feel good”. If you wait to bring up exit planning until you’re both fully comfortable with the idea, you may be waiting a long time.
I’m not sure how to raise the issue without it seeming forced . . .
There could be some variation depending on whether we’re talking about an existing client versus a potential prospect, but either way here are some questions to spark a conversation. You can begin by saying, “many of my clients say their biggest regret was being too reactive and not looking out far enough into the future. Would you be open to setting aside 30-minutes to start a discussion about that?”
Once you sit down together, here is how you might proceed:
“I know there are other things on your plate, but I’m glad you agreed to carve out some time to discuss the future. I hate to see clients miss out on opportunities because they weren’t prepared for them.”
“How has the course of your business changed from what you initially expected?” (follow up: What uncertainties do they have regarding the future?)
“What are your thoughts about your industry long term? What do you think are some likely opportunities and challenges in the next decade?” (follow up: What steps could they take to be better prepared?)
“What would you like to accomplish eventually?” (follow up: Can you help them reframe exit planning as a way to tackle unfinished business?)
“What options have you thought about for the eventual transfer of your business?” (follow up: Are they open to learning more about what’s involved?)
“I understand that selling your business isn’t on your radar right now, but would there be any harm in running some planning scenarios that include it in the mix?” (follow up: Which scenarios seem more likely or appealing to them? Are there other scenarios that they’re interested in protecting themselves from?)
There isn’t much I can offer so far ahead . . .
It’s easy to feel this way, particularly if your services are generally sought out a year or so before an owner exits. I’d like you to keep these two words in mind: Rethink and Refer. Rethink how you might broaden the timeframe during which you can be helpful. Think about all the mistakes you’ve seen owners make over the years, and how those could have been avoided. Package those insights into guidance they can use. It’s never too early to teach people how not to shoot themselves in the foot – even if it’s just in the form of a well-crafted whitepaper. The other thing you can offer is a thoughtful referral. A great benefit of XPX is that it makes it easy for you to build a trusted network of experts who can help your client with longer range planning.
I’m hesitant to ask clients to tackle something I haven’t fully addressed myself . . .
This is perhaps the most nuanced yet powerful obstacle many of us face. How can we ask an owner to start thinking 5-10 years out when, if we’re honest with ourselves, there are plenty of things we haven’t attended to. How many of us need to update our will, power of attorney, or health care directives; review our life insurance coverage; and so forth. Whether you are consciously aware of these unfinished tasks or not, asking our clients to look far down the road raises a mirror up to us, reminding us that we, too, have been postponing important planning.
If this resonates for you, consider leading with your own acknowledgment: “I know it’s sometimes hard to plan for things far down the road. I’ve been meaning to update my estate plan for a long time, and I just made arrangements to get that done.”
Responding to owner pushback
There is one more reason why some of us avoid having these conversations with clients: there is always the possibility that the business owner will reject our overture. They, too, tell themselves all sorts of reasons why they don’t need to contemplate their exit. Here are some examples of how you might respond to them . . .
Owner: There are too many moving pieces right now. Once I’m sure our new device is approved by the regulators, then I’ll have a better sense of our growth potential.
Advisor: It can’t be easy having that huge question mark out there. Exit planning is useful when there are uncertainties like that. We can map out options to help you prepare for different scenarios. If you wait until you get that approval, it may be too late to take advantage of certain strategies.
Owner: I don’t see the point in planning so far ahead. The market can change and that will dictate when I decide to sell.
Advisor: I can understand why you might not want to make plans if you’re not sure when or if they’ll be executed. But exit planning isn’t necessarily about locking plans in place; for many owners it’s about keeping their options open as much as possible. It’s o.k. that you don’t have a plan, but that doesn’t mean you shouldn’t begin to plan.
Owner: Stopping isn’t on my agenda. My father was miserable after he retired, and he got sick shortly thereafter. I won’t repeat that mistake.
Advisor: I’m sorry about your father. It makes perfect sense that you would want something different for yourself, but the best way to ensure that is by thinking ahead. Exit planning doesn’t require you to set a definitive date to stop working. What it does do is help you define optimal ways to stop if or when you choose to do so.
Owner: I don’t want to over-complicate things. When the time comes, I’ll use a broker. Once the business is sold, I hope to play golf and maybe doing some consulting on the side.
Advisor: I’m glad you’re thinking about what you want to do after you sell; that topic deserves plenty of attention. Exiting work on your terms (and feeling good about the sale price) positions you well to enjoy your next chapter. In my experience, using a broker will help you navigate many of the complexities of a sale. That said, there are numerous elements of your business that will determine its ultimate value. It can take time to put the pieces in place so that you can maximize your return. That’s where exit planning comes in. Can I give you an example?
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We have a professional responsibility to have these discussions with our clients and prospects, even if part of us would rather focus elsewhere. They look to us for our best judgement, and if we know that exit planning is in their best interest, then we owe it to them to introduce the subject – well in advance. Hopefully the ideas outlined above will help you initiate this important conversation with the business owners you encounter.
© 2026 Larry Gard, Ph.D. all rights reserved
