~by Haley Lynn Gray~
I’ve been in business long enough to make some spectacular mistakes, and to get a few things very right. These are some of the most painful lessons — the ones I’d most like to save you from.
1. Not being able to see the work
Early on, my team was spread all over the area and mostly working from home. It sounded lovely. In practice, it got abused.
I saw plenty of people reporting that they were being extremely productive. When I looked at what they’d actually accomplished, it was nowhere near what it should have been.
My first lesson at the time was “get an office early.” My view has evolved since then. Everyone wants remote work now, and it still gets abused — but the answer turned out not to be the building. It was visibility.
I’ve changed my model, because I now have much better tracking. When you can see what’s actually being produced — clear goals, measurable output, regular check-ins — it matters far less where people sit.
That matches what the research suggests. A large study led by Stanford economist Nick Bloom, published in Nature in 2024, found that employees working from home two days a week were just as productive as those in the office full time, and less likely to quit. The problem was never really the location. It was whether anyone could tell what was getting done.
The lesson: don’t rely on self-reported productivity. Measure the work itself, wherever it happens.
2. Not getting an advisor soon enough
I have an MBA. I have a lot of experience. I still should have listened to my advisor on several things much sooner than I did.
An objective set of eyes is invaluable precisely because it isn’t inside your head. It sees the thing you’ve talked yourself out of noticing.
The lesson: find someone who’ll tell you the truth, and actually take it seriously when they do. Good conversations with people who’ve been there are worth more than almost anything you can buy.
3. The wrong kind of advisor
Which brings me to the flip side, because it’s one of my most expensive lessons.
I’ve hired coaches who mostly told me what I wanted to hear — flattering, encouraging, endlessly positive — and charged a great deal for it, with no real benefit to me or the business. One of them cost me $47,500 in a single launch.
Flattery feels good and changes nothing. The difference between a good advisor and a bad one is whether they’ll tell you something you don’t want to hear.
The lesson: judge advisors by what changes because of them, not by how they make you feel. Here’s more on spotting the ones to avoid.
4. Being too nice
I’m not saying you should be unkind. But people have taken advantage of the fact that I’m nice — taking extra time off, not being as accountable as they should have been, pushing to see where the line was.
The lesson: draw the line clearly, and say something when someone crosses it. Being kind and having standards aren’t opposites. Most of my costliest leadership mistakes came from not looking closely enough, or not speaking up soon enough.
What connects them
Every one of these came from avoiding something uncomfortable: checking on people’s work, hearing unwelcome advice, spotting flattery for what it was, or confronting someone.
The discomfort doesn’t go away if you avoid it. It just gets more expensive.
I should have known better, in each case. But then, most painful lessons feel that way afterwards — which is exactly why it’s worth sharing them before you have to learn them yourself.
