Growing Your Leadership Team

Common mistakes and best practices

I’ve talked with many founders and CEOs recently about adding new leaders to their executive teams, and they have questions and challenges ranging from how to think about it in advance, managing the culture of the existing team with new leaders coming in, or dealing with lack of alignment on the other side of hiring great leaders last year. A few examples of the questions and challenges:

• Co-founders with a few employees that hiring fast and realizing they are going to need a few functional leaders to help manage some of those people

• Growth-stage CEOs with existing exec teams that need to further narrow the scope of those execs and bring on new functionally focused VPs, SVPs, or C-suite

• Large enterprise CEOs who expanded their C-suite and SVPs last year and now feels like they are not aligned

• A COO worried about the culture change of the first executive external hire in 2 years

• A recent executive who was promoted from within struggling with some management of former peers

Most of these questions and challenges are valid, understandable, and very predictable. They are predictable because they share the common thread of psychology, empathy, and human dynamics at work. Expanding (and/or upgrading) the executive team is eventually the right and best thing to do, but it requires the growth of the CEO and top team’s leadership muscle, awareness of the cultural impact, and a progressively stronger communication muscle. Below are a few highlights of common issues and best practices to prevent or address them.

Some (of many) predictable issues:

• You hire rockstars, they hit the ground running. You have a meeting a few months in and realize you are spread out like a starburst instead of weaving together like vines. One department and team has gone so far so fast, that one or two others feel completely out of the loop and frustrated by the misalignment.

• The first exec hire from the outside other than the co-founders hears from their team that they worry nothing will be handled within the team and everything goes to the founders anyway - disempowering the new exec and diminishing their ability to build a mini-culture and strong trust with their teams.

• Existing senior team members feel slighted and frustrated that someone was put in the next top spot instead of them getting the opportunity

• A new exec hire works at a faster pace with a different energy than the few other execs. While the goal was for that to be a rising tide that lifts all boats, it’s creating negative morale and frustration for the existing leaders and teams as it feels disjointed and not “team focused”.

• The CEO, COO, or co-founders feel extremely frustrated that some decisions are being made without their involvement, and as a result, are becoming a bit more controlling across the organization and seem stressed.

Helpful mindsets and best practices:

• Say Why - In the absence of alternative information, people come to their own conclusions. Every decision you make (or don’t make) creates a moment where someone on the team assumes “why”. The stories we tell ourselves of what is behind a decision or action are wild, rarely accurate, and often more negative than the reality. Don’t let them assume the rationale of big people or strategic decisions. Fill the void. In the restaurant business, we used to say, “a quiet kitchen is a crashing kitchen” - communicate, check-in, circle back, confirm, closeout.

• Trust - implied and earned - is the foundation of a great culture. Communication and connection are key components of trust. When you get busy with new execs, have new leaders leading teams, the cracks in communication get wider, faster naturally. You must bridge those proactively with additional check-ins and an improved communication cadence, at least in the early days.

• Friction - catch it! use the MMDD Log concept (Made My Day Difficult - see more here). As new leaders come, what also typically follows are additional new hires, new systems, and other changes deeply felt in the org. You’ll never anticipate all the pain points, but you can put in a process that catches them, allows you to identify patterns, and immediately address what’s addressable or explain and communicate what is not.

• Funnel Not A Tunnel - as your team expands, and they get their footing, the founders, CEO, COOs, etc. have a bit more time to think - but your team doesn’t always enjoy this dynamic. When the top leaders start sprinkling their new ideas all throughout the organization, a well-intended set of inspirational interactions can become huge distractions for the team and big frustrations for the new key leaders.

This is all a reminder that every time you grow your executive team, YOUR job as CEO, COO, founder, or top leader also changes.

Ask yourself - now that I have this evolved team, how should my role change? Answer candidly. Act on that. Make the changes necessary each time your team grows, so you get the benefit of their presence and they thrive in your growing company.

If this topic feels relevant, we’re talking about this and more topics on leading through change in tonight’s 75-min Leading Through Change workshop on Bright at 8pmEST. You can register here Leading Through Change Workshop on Bright - share the link and join us!