How to lead, pivot, and evaluate talent. 3 Questions, 3 CEO's.

Now is a time where we should all be really open to new perspectives on leading, talent management, and vision setting. The question is where to look for inspiration? I think we all should look to start-ups and agile technology-forward companies for wisdom. Big companies have a lot of great advantages, but they also suffer from too many sacred cows. I had the chance to ask a few amazing CEO’s a few key questions that I think will provide huge value to this newsletter base.   I found inspiration and take-home value in their words and think you will as well. Hamilton Powell is CEO of Crown & Caliber (www.crownandcaliber.com) a fantastic online solution for buying and selling watches, Stephanie Nadi Olson is CEO of We Are Rosie (www.wearerosie.com) a modern talent company, and Eran Gil is CEO of AllCloud (www.allcloud.com) which combines an expertise of cloud integration with custom solutions across top technologies including AWS, Salesforce and NetSuite. They are all plain spoken and super thoughtful. Have a read...

Question 1: What is the most important thing you look for when making a senior hire, especially during a time of chaos/challenge where every move counts for so much? 

Stephanie (CEO of We Are Rosie): It's all about mindset. When making a senior hire, I look for what I've termed a "strategic rebel". This is someone who has true expertise in their field, and who will bring that domain knowledge, plus a rebel-POV. I want someone who will look for conventions we can break and norms we can flip to move the business forward in innovative ways. I want someone who won't settle or accept the norm. This is particularly important during a time of crisis. I am a firm believer that crisis always makes way for incredible growth.  

Hamilton (CEO of Crown & Caliber): At Crown & Caliber, we live and die by our values. Its how we find meaning in our work. So, we hire based on them. We fire based on them. We recognize, reward and celebrate when team members exhibit our four values: Act Like an Owner, Move Fast, Better Together, and Love People. We realize that our Values are the means by which we achieve our Purpose: “To leave a positive and lasting impression on the lives we intersect.”

So the #1 thing we look for when hiring anyone (not just a senior hire) is whether they can demonstrate our Values and are aligned with our Purpose. Our best hires have been those who are completely in sync with this. They find meaning in their job because we are all rowing the same direction. Our worst hires have been individuals who are not aligned with our Values and Purpose. They aren’t rowing in the right direction, and ultimately they are just as miserable as we are. It never ends well.

Specific to senior hires, I have learned to distinguish between management and leadership. The two are very different, and I think a time like we are living today (COVID) really brings out the difference. I can sum the difference between management and leadership in one word: Uncertainty. Managers must produce. Leaders, however, must use imperfect data and uncertain outcomes to make decisions. This is certainly the case in a start-up like Crown & Caliber. And it is definitely the case in a post-Covid world of uncertainty. So, specifically the thing I look for when hiring senior managers is their ability to make decisions in the face of ambiguity.

Eran (CEO of AllCloud): Experience. That may seem obvious but specific experience dealing with challenges, and experience at failure is important. Leadership when things are going well is easier, but leadership during challenging times is difficult. Leaders who have been through significant challenges, and experienced failure are better equipped to face such events/time without cracking under the pressure; to make critical decisions without panicking; and to help push an organization through the tough times. During challenging times, the best negotiators or technologists are no match for a leader that has been in the foxhole and survived the war (I subscribe to the war-time CEO concept by Ben Horowitz).

Question 2 - If you are thinking about making a change to your business (aka - some pivot), how do you go about that process?

Hamilton (CEO of Crown & Caliber): Early on in our business, we would make decisions in a “ready, fire, aim” manner. And that is exactly the right thing to do in the early days of any start-up. Damn be the consequences. Make a decision or run out of cash. Its pretty simple. We had bean-bag chairs. Take that big companies! 

However, as we started to grow, this knee-jerk decision-making style gave rise to what many at Crown & Caliber dubbed: “The Good Idea Fairy”. It’s a way of saying that I was creating all of these ideas, and giving no thought to the consequences of our team. Patrick Lencioni said: “If everything is important, then nothing is”. So, we needed a process through which to make decisions. Something that took the entire organization, our goals, our capital, bandwidth, etc into consideration. I hated it. I thought we had become bureaucratic. We might as well have become the DMV. 

So, we adopted a decision operating system called EOS (from the book titled Traction). It was awesome. Difficult and sometimes painful, but awesome. Essentially every project we did had to first be filtered through three major “fit” questions:

1.      Strategic Fit: Does this project get us closer to our Vision and our 3 & 10 year goals?

2.      Economic Fit: Is this the best use of capital?

3.      Effort Fit: Do we have the organizational bandwidth to do this? 

I can say that without this decision-making process, we would still be a small, over-worked start-up. I would still be on a pirate ship. It was a major part of our maturing process. 

Question 3 - What is one people management lesson you have learned the hard-way?

Eran: Communications are all about positioning, and many times sets the tone and the culture of the organization. Candor balanced with empathy is of critical importance. It may seem easier at the time to sugar coat bad news, but a direct/ transparent conversation will be more beneficial to employees in the long run. Facts are important, but delivery of facts in a manner that is understandable is even more crucial. 

Stephanie: The biggest lesson I've learned is that the assumptions we make about career trajectory being linear and hierarchical is holding people back. To illustrate with a personal example, I do not thrive while managing people on a daily basis. I thrive while leading a team, setting the tone and values for the organization, and establishing the vision and opportunity we can all work toward. This skill-set is quite different from setting quarterly and annual personal goals, evaluating attainment of those goals, performance conversations, etc. I used to think that I had to be good at all of it because of the hierarchy of leadership framework I've been taught my whole life- you can't lead an entire organization until after you've managed people. The lesson in all of this is that we should question the assumptions we make through the hierarchical career trajectory in corporate America. Perhaps the logical next step isn't to go from really good contributor to people manager in every instance.

Too often, people look to Fortune 500 CEOs for inspiration. I just dont believe that for most of us, that translates very well. Eran, Stephanie and Hamilton on the other hand offer tangible and real advice for us all to find inspiration. I am lucky to know them and hope you found it interesting as well.

Please like, and/or subscribe to this newsletter if you enjoy what you read today. Join 28,000+ others who have already given it a follow. I promise you it will be useful, plain-spoken and not preachy. Would also love to hear how you are leading, pivoting, and evaluating talent. Hang in there everyone.