Leadership Lessons: How to Ask for Help
One of the mistakes I made early on was surrounding myself with people like me. It’s difficult to break out of this silo. You go to college, and probably end up hanging out with friends from a similar background. Then, when entering the business world, you do the same. Not recommended. The last thing you need is more of yourself, right?
If you’re a leader and want to be a good one, you need a ton of help. As a Founder and CEO, I want to learn from others because I believe it will make me not just a better executive, but a better person. But how do you find the right people to ask? Don’t get hung up on formalizing a “personal advisory board” — let it evolve naturally over time. Here are a few pointers I’ve learned along the way.
Diversity (of POVs)
I’m a big believer in seeking multiple perspectives. There are many people I turn to when mulling over an idea, looking for fresh opinions, seeking diverse inputs. Some of them are in my industry, they’re former colleagues, fellow CEOs, current executives on my team, or peers from wider networks. But I also draw on the experience of those not in my immediate work circle, because many times those conversations generate more interesting and different avenues for me that can be invaluable.
For example, my wife is a highly-trained school psychologist, focusing on children with special needs. There’s zero overlap between her work and mine — and yet she’s one of my go-to people because she’s an unbelievable sounding board, and I value her take on everything.
Most of us have somebody in our life that we trust implicitly, but because they don’t work in the same field as us, we probably don’t ask about work stuff. In my view, this is a mistake. Start asking, you might be surprised by their fresh ideas, especially if you’re feeling stuck, or overtired. It’s energizing to see things from a different angle.
Walk (and Listen)
When I walk my dog I like to get new insights from business books via Audible. This enables me to easily learn and think without taking the extra time to do so.
Recently I’ve been listening to TRILLION DOLLAR COACH, The Leadership Playbook of Silicon Valley’s Bill Campbell by Eric Schmidt, Jonathan Roseberg and Alan Eagle (2019, Harper Business). Campbell was a crucial behind-the-scenes mentor to many famous Silicon Valley entrepreneurs — including Apple’s Steve Jobs and Google’s Larry Page. His approach was instructive, he helped founders focus on what’s important, to double-down on asking questions, getting a wide variety of opinions, and seeking buy-in. This book has inspired a lot of ideas for me.
I also enjoyed The Goal by Dr. Eliyahu Goldratt (1984, North River Press). Dr. Goldratt was a physicist-turned-consultant to many of the world’s largest corporations, including General Motors, Procter & Gamble, AT&T and Boeing. Best known for Theory of Constraints (TOC), Dr. Goldratt’s book is a rich allegorical tale of business highs, and lows — but he also goes right back to Socrates, and the birth of rhetoric, forming an argument, and resolving difficult situations. Again, his perspective gave me some new views I could use.
Now I found out about both of these books through personal recommendations, because I have a semi-formal “book club” relationship with people I trust. This is an invaluable way to expand your knowledge base — especially if you bring different perspectives to the books you’re both reading.
Treat Your Team as Equals
A lot of CEOs don’t ask their C-Suite for insights, because they feel compromised. After all, your direct reports are beholden to you for their salary and position. But at Apptopia I treat my team as equals and am willing to show an unbelievable amount of insecurity when seeking their input. These are smart people and I hired them for a reason.
I recommend going to your team even when you think you know the answer. Maybe you’ll get validation and that’s great. But you might get a whole new angle, and that’s even better. I feel that the more you talk about something, the clearer the picture gets. Keep iterating, keep asking for guidance, push yourself. Your own conviction might be drowning out the truth.
Don’t do what I used to do and make a snap business decision because you’ve got a gut response. Vet ALL ideas. I’m the CEO of a 100-person company. Within a few hours I can get a lot of good opinions. Demonstrate maturity by asking for help. After all, a bad decision takes a lot of time — and money — to unwind.
Talk, Don’t Text
Please don’t hide behind the Slack channel or other tech-based mechanisms. Pick up the phone. I have learned that a frank phone call does wonders when I’m unpicking a problem. It better grows your relationship to speak live with other humans and the chance of miscommunicating is significantly decreased. Plus, you’re more likely to get the person’s undivided attention. There’s so much more context you can obtain when talking live. Try it.
Every leader needs a sounding board, someone who has their back, providing honest, constructive and timely feedback. Yet the higher up the ladder you go, the harder it is to find such a person, or persons. Without genuine support, leaders exist in an echo chamber and cease to grow in effectiveness. I feel I’m a better CEO because I have a lot of people in my corner.
