Culture-Focused: Leadership Development

Ok, so now you know what to look for in a COO. Maybe you already have that process-oriented partner who handles the team and system development. Maybe you ARE the COO, the person responsible for a growing team and an evolving service set. How do you know when it's time to not just delegate day-to-day tasks, but leadership responsibility?f

As OMG grew, my self-mandated weekly 1:1 check-ins with each team member became too time consuming to actually get the work done that came out of those check-ins, not to mention the operations and big-picture team development that is needed. Biweekly seemed to work all right, but continued team growth started putting a strain on my time once again. It took about a year and a half for the consideration of adding another level of management to our very flat organization started to shift from a future potential into a rapidly growing necessity. 

Understand Your Purpose

When we first established the Director role at OMG, I wasn’t sure if I was cut out to be a leader of leaders. I was used to managing a team of 30+ by having one-on-one conversations with each team member and running collaborative departmental and group syncs. I wasn’t sure if I was communicative or expressive enough to share everything I was thinking and planning clearly enough to trust a middle-man to take it to the larger team. I wasn’t sure if having a middle manager was going to actually add value, or instead create inefficiency and delays.

The truth is, during that year and a half, I was terrified to delegate leadership responsibility. I was worried my standards for myself as a leader would not be practiced with the same level of commitment and dedication by others. I was nervous that the correct priorities would not be clearly communicated to the team. I was hesitant to trust anyone else to be as great a leader as I was, for this team. Yes, I know how that sounds, but hear me out. The team at OMG is phenomenal and deserves leadership who cares about them individually, personally and professionally, and will be a voice, an advocate and cheerleader for them. The clients of OMG expect leadership committed to excellence in care and competence and unwilling to accept any less from the team. The culture and environment of OMG requires leadership that is willing to speak up to protect and improve when normal day-to-day operations and interactions threaten to break it down.

Despite my reservations

It was quickly becoming clear that I couldn’t continue to be all things to all people, and in fact already wasn’t. I couldn’t move company-wide initiatives and operational updates forward as quickly as I wanted, and I could no longer meet with each individual of the team as often as they deserved. In fact, the team was already finding other people that they trusted to give advice and insight to their day-to-day situations, rather than relying solely on me. It was time to move into the next phase of growth, personally and professionally, necessitated by our progression of growth as a company. If I was going to continue to deliver the most impact to the team and organization, something had to change.

Because of my concerns, I probably waited a little longer than would have been ideal to develop and assign director roles. However, that extra time allowed me to solidify the vision for the role, both in terms of responsibilities and relationship with me, and make sure the new directors would be set up to succeed in that role, rather than set up to fail. It also allowed for the right pieces to fall into place to promote veteran team members into those roles with full confidence, not just in their abilities and alignment with the vision for the role, but also confirmation that the team was bought into them as a new direct report.

The good and the bad

A few things we learned about setting people up for failure in leadership roles:

  • Make them a leader in name only. Don’t establish a system of accountability. Allow circumvention of the leader.
  • Reserve clarity. Vague responsibilities of the leadership role or of the team members who report to the role. Don’t clarify to the team who their direct report is and how that affects their day-to-day.
  • Save the things. Don’t bring up anything in the moment, but pull it all out during the annual review. Especially things other people brought to your attention so you don’t have first-hand knowledge. 

A few things we learned about setting people up for success in leadership roles:

  • Systematize leadership. Make the delegation of leadership abundantly clear and hold people accountable to work within the roles and systems established. Direct all conversations to start with the new direct report, no leapfrogging to you. Check in weekly with your new leaders, and have them check in weekly with their direct reports
  • Give all the clarity. Make the implementation of leadership very transparent. Share the role expectations and responsibilities with the entire team as a group, and individually as it pertains to them specifically. Explain how this affects your role and how it will change your schedule and conversations.
  • Say the things. Promote trust and confidence in the care and competence of the person taking your place in their day-to-day. Don’t wait to ask about anything you notice in the day-to-day or that is brought to your attention.

A few of my favorite leadership tools:

  • 1:1 check-ins. There is no better way to build trust and connection than a weekly 15 minute check-in with your individual team members, and the insights and improvements that you’ll gain will be invaluable.
  • I highly recommend the book Radical Candor by Kim Scott. Business IS personal! I became a better boss OVERNIGHT after reading this book. Having my leadership team read it and then presenting the core concept to our team at our 2020 annual summit impacted the way everyone functions and communicates.
  • The Global Leadership Summit is an annual event that we've participated in for the last six years and is always very helpful in developing leadership skills across the team. 
  • I also recommend the book A Freethinking Leaders Guide: 9 Lies About Work by Marcus Buckingham. This book proves the issues I’ve had with “normal” management standards were legit and gives real, “normal” solutions.
  • We use Culture Index as a screening tool for all candidates. It has a pretty hefty annual fee, but it pays off very quickly in terms of making sure you're hiring people who will be naturally inclined to the role you want them to fill. It allows you to focus your interview process on evaluating culture fit, already knowing they’ll be a good job fit.

Final Note

I am very hesitant to hire from outside for leadership. I want to be confident that before I assign authority and autonomy that there is alignment in culture values, company vision and goals. If you have people you can evaluate internally I'd start there, but obviously we all had to get hired at some point. The guys had no idea what they'd be getting from me when they hired me as a part-time, remote bookkeeper. I couldn't have begun to imagine what we've become either! So if you already have team members you can consider, strongly evaluate that, but also if it's a no, don't do it just for a short-term fix.

If you are leading with character and candidness, and expect your leadership team to do the same, once you have the right people in the right seats I am confident you will have great success. 

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