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Scaling Leadership (Sharon Richmond) Transcript

To Lead is Human – Episode 43

Scaling Leadership (Sharon Richmond)

Sharon Richmond: Sometimes, we get the feeling that we have to compare ourselves to others. And I guess for that point, I’ll say, the best advice is keep your eyes on your own paper and compare your own leadership to yourself.

I’m Sharon Richmond, and this is To Lead is Human. For more than 30 years, I’ve run a business called Leading Large. I coach C-level executives to expand their impact. They clarify their development priorities. They energize their organizations and they build cultures of accountability and respect.

In this podcast, we usually focus on helping you to envision how to improve your own leadership by introducing you to other executives who have walked the path before you. They’ve learned firsthand that the positional power their role affords them comes with an equal measure of personal responsibility. Today, however, instead of interviewing one executive, I want to share with you some of the key topics from a recent conversation I had with a group of CEOs of mostly early stage companies, although not entirely, as they talked about how they’ve worked on scaling their own leadership in their organization, especially in high growth mode.

Brené Brown has been quoted as saying, “A leader is anyone who takes responsibility for finding the potential in people and processes, and who has the courage to develop that potential.” I share this quote with you today as a reminder that it will take many leaders in your organization to achieve this goal. In the beginning, it can be just you. But as you grow your organization, meet other leaders to help you not just find the potential in the people and processes, but develop them. And that is why it matters that we focus on scaling leadership.

Of course, the best time to think about how you’re going to scale leadership is before you hit that stage. In fact, one of the most challenging aspects of scaling a leadership is thinking about it far enough in advance to make sure you get a solid foundation in place. There are a few challenges that get in the way of thinking about scaling leadership. And just in case you might be feeling any of these emotions yourself, I’m just going to list them out briefly.

Internal competition. Is it hard to give away credit? Are you feeling a little bit competitive with your colleagues? It’s natural and normal to feel this way, but not helpful when you sit in the top chair.

Fear and insecurity. We all have it at times. And of course, the best way to overcome your insecurity is to be unashamed to ask about what you aren’t sure of. So try to talk with your colleagues early on about things you’re not quite sure about in terms of how to lead them.

And then, of course, the third thing is, sometimes we get the feeling that we have to compare ourselves to others. And I guess for that point, I’ll say, the best advice is keep your eyes on your own paper and compare your own leadership to yourself.

So let me talk with you about three developmental stages of scaling leadership. The first is scaling yourself as a leader. And there, I would like to invite you to think about, maybe even analyze, the time horizon of what you’re focused on. Take a sample week and think about how much of your week are you spending focused on relatively shorter term issues, challenges, and decisions. Let’s say one to three months.

In the early days of the company, such work is the proper focus of the senior executives, along with, of course, making sure you’ve got money in the bank and customers who will pay to buy your product or service. In this stage, executives have typically held decision authority for themselves, and most interactions take a hub and spoke structure with the leader at the hub, approving strategies and plans and sometimes even tactical priorities week to week.

There is a stage at which you’re going to start hearing your team ask for some repeatable practices. Can’t we do this the same way we did the last one? More clear goals. Let’s really say what numbers we’re trying to hit, in which areas, and also performance feedback. How am I doing in my job?

Your team members need all of these in order to stay aligned and focused so they can guarantee delivery of what a company must produce. So most of the CEOs in my conversation agreed that it can be personally hard to let go at this point. Knowing this in advance, I invite you to think about how can you prepare yourself to share decision responsibility at a pace that you can manage.

The second aspect of scaling your leadership is your team. And here, the decision is, do we build the skills internally or do we buy, meaning, do we hire from outside? As an organization grows, achieves product market fit, you see that you must develop other leaders, as the needs of the organization change.

The organization now needs functional leaders who can successfully scale their areas, can make good decisions about how to grow sales, product development, people operations. And each of these leaders needs to have clarity about what they can decide in their functional area and when they need to come back to the team for alignment or even approval. This means you as the chief executive need to ensure a clear strategy and that the leaders in your team can provide focus, priorities, and define the objectives to which the company is committed.

At this stage, you also need your leaders to be able to select new employees, well, onboard them and develop their team’s capabilities. As you reach this stage, you will have to think about the trade off from growing within to hiring outside. And some of this will depend on the skills of your founding team.

A particular dilemma that often comes at this stage is, for example, staffing leadership in a function that you have not well developed early on. Let’s say bringing in a chief people officer or a head of people or a head of finance, an area that hasn’t really had much investment up until this point. And certainly, I have seen at a number of clients over the last four to five years that that first executive hire is challenging, not so much for the employees of the organization, but for the executive team, as we are forced to reexamine the norms of our team.

The third iteration of scaling. I’ll call it the professional management stage. And this will depend. Sometimes the executives you have in-house have all the capabilities you need to continue to grow and scale, but at some point, you may face pressure or find a need yourself to bring in an experienced executive or two, and particularly to bring them in above your existing managers, the ones you’ve grown in-house.

As you can imagine, this stage of scaling can be really challenging. Emotions tend to flare. Early company employees sometimes feel overlooked or less respected, especially if they’ve been promoted once or twice but aren’t quite ready for that higher level role. Use your most skillful relationship management and more active listening than you ever wanted to do as you hear people out, affirm the concerns that you hear and help them see that there’s a good way to move forward with increased expertise in their area. Do that listening and you’ll uncover potential risks that you can mitigate, whether strategic differences among the team or work style differences that come to the surface.

One especially useful tactic at this point is to make sure to include the people who will be reporting to or collaborating with the new executives during the hiring process. Obviously, make sure you’ve got some good candidates, but maybe take the last three candidates and invite others to be part of the interview process. It may take a little longer up front, but you will find the benefits as your current employees begin to look forward to having someone work with them who can better help them grow their own professional skills.

Another thing that happens in this stage is that internal partnerships become more and more important during scaling. And it’s especially key that marketing, sales, engineering, R& D, back office functions all know each other’s priorities and support them and that they can identify any misalignments and take quick action to unblock bottlenecks.

If you want to think about some ways that you can help ensure that your leadership team scales and helps you stay one or two steps ahead of what your organization needs, here are a few tips. First, every time there’s a new addition to or a change to your executive team, bring the team together and take some time to reset expectations and norms so that you are building strong foundational relationships with each shift.

The second thing is, and this is not just for newly hired executives, but for all of your executives, take care that you are clarifying detailed mutual expectations. What will each executive be accountable for? Nothing will damage that new relationship faster than misaligned expectations or unclear agreements. And nothing will help you ensure accountability better than aligning with your colleagues to make sure everyone knows what they’re accountable to deliver, what decisions they’re authorized to make, and how the team will work together to bring the organization to its next level.

The typical challenges that executive teams face across all the high growth stages and need to be thought through at each of these three different stages of scaling leadership include maintaining focus, aligning cross functional priorities, providing adequate transparency so the organization understands where it’s going and how to get there and developing other leaders. Thanks so much for joining me today for this conversation on one of the biggest challenges an executive faces as you are scaling your company.

I’m Sharon Richmond, and this has been To Lead is Human. You can find out more about me at That’s L-E-A-D-I-N-G large dot com. To Lead is Human is part of the Mirasee FM podcast network, which also includes such shows as Just Between Coaches and Making It.

This episode was produced by Cynthia Lamb. Danny Iny is our executive producer and post production was provided by Marvin Del Rosario. So you don’t miss upcoming episodes, please Mirasee FM’s YouTube channel or your favorite podcast player.

If you gained a useful insight today, please tell one of your colleagues about us and invite them to join in at the next episode. And take a minute to leave us a starred review. As it turns out, that really does help us reach more leaders. And as far as I’m concerned, the more leaders we reach, the better for all of us. Thanks so much for listening. And I’ll see you the next time on To Lead is Human.