Insights, advice and mentorship from people leaders to help navigate the challenging & rewarding "messy middle" between Product-Market Fit & IPO

How to Launch Management Training for New and Emerging Leaders

Just because someone has the title doesn’t mean they’re a competent leader. That CFO buddy you hired just out of college was great during the startup phase, but are they ready to lead a department of 50 people?

Many growth-stage companies struggle with the “buddy-to-boss” transition. There are a lot of junior leaders brand new to the manager role. They may be energetic and hungry, but they’ll need time to learn the skills necessary to lead, nurture, and even mentor their teams.

In the latest interview for our Startup to Scaleup series, people leader and advisor Beth Steinberg covers how to introduce an effective leadership development program. With two decades of experience under her belt, Steinberg not only shares the practical steps to implement management training, but also the cues to recognize when outdated leadership styles need a refresh.


Steinberg is currently VP of people and talent at Chime as well as the founder of Mensch Ventures, a startup advisory firm out of San Francisco. She’s held the Chief People Officer role at Zenefits and Madison Reed. She is a certified coach and has a degree in clinical psychology. The following interview has been condensed and edited for clarity.

When is it time for a company to put management training in place?

I would highly advocate very early on to have coaches, even when there’s just a founding team. But in terms of having a more comprehensive leadership development or management development offering, I think you start as early as you're able, meaning you have the capacity to either do the training yourself or partner with companies like Strive.

There is no question in my mind, the earlier you can build management and general leadership capabilities and competencies, the better time you are going to have scaling.

I characterize leadership and management development as a core part of gracefully scaling a company.


How do you convince a reluctant CEO or leader that L&D is something companies should invest in?

When people are having issues getting the support and budget for leadership development, I counsel them to do some no-cost exercises, then amplify the results. For example, get a group of leaders to read an article about leadership or management, then have an open discussion around that article, how they can apply it to their day-to-day. And 100% of the time people will come out of that meeting saying, ‘That was amazing. Can we have more of that?’ You will get a ground swell of people to get the funding. And I do think it's changing. More and more leaders understand this is a business imperative, but it's still not ubiquitous. We've done a disservice to so many tech companies by pretending that leadership was just something that came by osmosis, because you were anointed a leader. We have this expectation that a CEO knows how to be a good leader, when oftentimes it's their first experience and they've never had any training.

Leadership and management is a skill, a craft, and a competency. It doesn't just happen by chance.

Should a company build management training and leadership development in house or use an external vendor?

I'm a big advocate of doing both. Some things I like to do myself. I like to be the voice from a cultural perspective. But you also really have to understand how to build a curriculum. Very few chief people officers are instructional designers. Also, are you a good facilitator? Do you understand the appropriate steps of practice and feedback? You've got to be real with yourself and ask, ‘Am I even capable of doing this?’ From a practical perspective, myself and my team are not the experts on everything. We don't have the time right now at Chime. We have well north of 125 people leaders, and leadership development is a full time job. So I really make the calculus of what's going to serve our leaders better: to do this ourselves or to engage with a trusted partner.

If you decide to bring in a partner to help train and develop leaders, how do you decide where to start in an organization: senior or newer managers?

Especially in a resource-constrained environment, you have to make that determination. Now, my thinking has really evolved on this, but I start with first-line leaders. They are your biggest touch points in terms of leadership within the company. Typically they hire the most people, they have large teams, they're often new to this, and this might be their first or largest job. To not have them competent and confident is a big risk to the business. So I always start with first-line and then work up from there.

What are some of the most common pitfalls or mistakes companies make with management training and leadership development?

The biggest mistake I've seen is too much focus on classroom learning. I didn't really fully understand until I started studying neuro-leadership and neuroscience, but there is a real way the brain learns and absorbs things, and if you are sitting in a semicircle lecturing to somebody with a PowerPoint, with no dialogue or practice, it hinders people's ability to absorb and practically use that information. What I look for is companies that understand how people actually learn and get results.


What do you think are the most important skills for new managers to focus on developing?


Leadership is evolving. Now the most successful leaders are those who can be vulnerable and transparent.

The model of command-and-control is no longer an effective leadership style. So one thing that is critically important for people to learn is to incorporate self-reflection into their own leadership style. Because oftentimes we skip that step; we don't get people to think about their own strengths and opportunities. Furthermore, it’s important to teach people how to be effective communicators, to give and receive feedback, to be good storytellers, to have an eye and be builders of talent. All of those things are critically important, but in order to self-actualize, you need to start by looking in the mirror.

What is it about your work you find most rewarding and inspiring?

There's no question that what I find most rewarding is being able to help people succeed. Both in bringing talent into the company and helping people learn and grow in service of meeting our business objectives is very inspiring to me. A lot of our work is really the long game. Sometimes it might take six months or a year to see the results. But all of the work, for example, that we did around building leaders is now coming to fruition as we're more able to scale the company and we have more confidence in our ability to do so.


What have you found to be most stressful or challenging across your career as a people leader?

The most stressful periods for me are when situations are not aligned with my own values, where really challenging things are brought to you and you have to be able to put your own personal feelings aside and try to do what's right for the company and for the person. And that can be really hard. I'm sure every people leader has come to a point where they had to look in the mirror and say, ‘Is this really who you are and who you want to be?’ And I've had to do that many times. That is the most difficult part of this job.

Talk about that self-learning process a bit more. What does that look like?

Especially when you're the most senior person or when you're in an emerging company and you might be the only person, it can be a really lonely job. You don’t want to talk to other people about some of this personal and ethical stuff that might be going on in the company. But I am very lucky to have an outside group of people, coaches, or other chief people officers who I bounce things off of. We stay very connected on things like this. And as I've grown and matured, I know what is important to me and what's not important to me; I've developed that over time.

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