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Why the “best” advisors should be fired (plus 3 tips to picking the right one)

If your trusted advisors have not pushed you out of your comfort zone in the last year, you are working with the wrong people. That means you ARE missing opportunities and leaving money on the table.

I have seen it time and again: business owners, presidents or CEOs that are in love with their advisors for the wrong reasons. The relationship is easy; they are buddies and there is no discomfort.

The recipe works for awhile, sometimes a long while – until it doesn’t. Usually it comes up when the company is considering selling itself or when there is a material lawsuit or when you receive a letter from the IRS informing you that you have been selected for an audit.

The best case scenario would be the IRS completing its audit and concluding the company is compliant. (Please note: that doesn’t mean you are minimizing your tax liability. The IRS will not inform you of extra credits or deductions you could have taken.)

Here are some other scenarios: you get fines and penalized by the IRS, you are unable to sell your business or you have to sell it for a lot less than you expected, the cost and/or judgment imposed by a lawsuit bankrupts your business.

Am I suggesting you hire a person who annoys you? No. Part of the selection process for your trusted advisors is selecting people you want to work with, people you respect, and people who have complementary skillsets, abilities and areas of expertise. I am, however, suggesting you skip the feel good advisor who just appeases you and tells you what you want to hear.

Here are three tips to selecting a great advisor:


Good advisors will at some point pick you apart until there’s nothing left. That’s a good thing. Compatibility is one thing. Having people so accommodating they do you a disservice is another. Advisors who don’t ask challenging questions hold your business back. The key here is to lean into the discomfort. Check out this amazing TED Talk about daring to disagree.


You want someone who is principled and who thinks of the big picture for you and all your company’s stakeholders. A good advisor risks at all times NOT to be your advisor. Make sure you are surrounded by people who are not afraid of losing popularity.


Talk is cheap. Measure results. It is simple. What did they promise, what was delivered? The numbers never lie. Maybe you will measure your profits, maybe customer satisfaction, maybe it is turnover. There is always a way to measure what you are getting from your consultant.

Cards on the table, I get the naysayers. Why pay someone to come up with solutions you already know. We are expensive. We usurp your time. To you, we are risk from day one. But if you pick the right advisor by your side, you’re going to make more money and be better protected. Your business is going to go further and faster. You will know you made the right and best decision 100 percent of the time.

And if you feel like firing them some days, even better.


If you have never been upset or challenged or had an impulse to fire your advisor, you haven’t had the right advisor. Sooner or later, it will fall apart. Worse, you will leave money on the table.