The Problem with Advice

Four Reasons I Stopped Advising and Started Coaching

When I joined Slack back in the summer of 2014, an odd thing happened: strangers started asking me for advice. So I embraced it: helping these ambitious strangers felt right. When I left Slack a year later, I assumed that was all over. But I decided to write about my experience so I could share what I had learned. Suddenly more people than ever were asking for advice: not just strangers on the Internet, but the fine folks at First Round Capital, Flybridge Capital, Acceleprise and others. I embraced not just advising, but being a consultant, advisor, and mentor full time.

It took becoming an advisor to truly understand the problems with advice. But it also showed me the solution: I stopped advising and started coaching. In lieu of arming myself with answers, I armed myself with powerful questions, aimed at unlocking the answers already within my clients. There was no going back once I saw the difference between the advisory and coaching mindsets—and the powerful results coaching delivered for my clients.


Advice Is Narrow

As an advisor, I was often asked the obvious question first: “How did you do it at Slack?” I seldom answered it without heavy qualifications: despite Slack’s success, the chance that our decisions would be right for another company were close to zero.

No matter how they state it, advice is based on the advisor’s personal experience — and thus limited by it. Just because it worked for them, their company, or their colleagues doesn’t mean it will work for you. Was their role the same? Was the company the at the same stage, with the same culture? Do they have similar personalities, strengths, and weaknesses? Even if their advice carried them to great success, it’s likely their context is more different from yours than it is similar.

Now as a coach, instead of explaining what we did at Slack (or avoiding the question), sometimes I’ll share how we decided and why. The person I’m sharing with can find their own lesson in the story, judging for themselves its true relevance. No advice necessary.

Advice Is Someone Else’s Idea

As an advisor, I was sometimes asked to help my clients take action. “How should we handle this situation?” “Do you have a playbook?” “Can you propose a plan?” Yet few fully followed my recommendations.

In retrospect it wasn’t surprising: would you really execute someone else’s plan without making it your own? Even if a given morsel of advice beat the odds by proving its relevance and motivating action, you’d still never follow it exactly. “Taking” advice usually means breaking the advice apart and building your own plan with the pieces.

So why not start with the plan instead of the advice? Now as a coach, I begin with my clients’ vision for their future, and together we build a plan to get them there. Maybe my advice will come up, maybe it won’t. What’s important is the plan is 100% theirs—that gives it the best chance of becoming action.

Advice Inhibits Exploration

As an advisor, certain people approached me looking for an easy answer, looking to save the time it would take to find their own. “What’s the best practice here?” “Can you make a recommendation?” If my advice didn’t resonate, it would awkwardly end the conversation before we had a chance to explore other solutions.

Now it reminds me of the classic science education exercise, the Egg Drop Challenge, where students build a container to protect an egg being dropped from a given height. Why not just give each student a sturdy box full of packing peanuts and call it a day? Because it would end the conversation before they had a chance to explore other solutions, just as it did for me. The Egg Drop Challenge isn’t about saving eggs, it’s about finding your own path. And you can’t find your own path from advice any more than you can from a box full of packing peanuts.

Now I start with powerful questions, not answers. “How will you know when you’ve found the right solution?” “What will it take to get you there?” “What will it mean when you arrive?” As a coach, I trust that my clients have all the solutions, I just create an environment to draw them out.

Experience > Advice

As an advisor, those who sought me out did so because of my experience, as a product leader at Slack and as a startup founder. “I admire the work you did at Slack, I’d love to learn from it.” But was advice really the best distillation of that experience? I don’t think so. I don’t mean the experience wasn’t valuable—I mean it has yielded much more than advice.

As a coach, my experience lets me understand my clients more deeply, helps me build empathy with them, and gives me more perspective on what they’re going through. When they finally earn the full trust of their CEO or their board, I don’t need endless explaining to know its implications. When they share their career ambitions and their fears, I can be their champion without blowing smoke: if I say they can achieve their dreams, I really mean it. Today my fulfillment comes not from giving advice, but from building a strong connection with clients, and helping them succeed beyond what my advice ever could have enabled.


Now for Some Advice

First, I fully acknowledge the irony of giving advice to avoid advice, especially on Medium, the premiere advice platform! But I’m not suggesting we entirely avoid it, of course. I am suggesting that we look more closely at what purpose advice really serves. When we ask for advice, is that truly what we need, or is it another kind of support? When others ask us for advice, how can we truly be most helpful?

When I took my first coaching class, the suggestion to stop giving advice seemed extreme. Absurd, even. But having embraced it, I know I’m helping my clients more as a coach than I ever did as an advisor. Want to learn more? Please feel free to get in touch.