Succession, Scale, and What Young People Actually Want with Diane Tavenner

Diane Tavenner has done the thing most founders talk about and few do well: she built something, grew it, and handed it off cleanly. Then she started over.

Diane co-founded Summit Public Schools, scaled it from one high school into a network across California and Washington, transitioned it to a successor, and is now CEO of Futre, a platform helping young people figure out what comes next. She joins Christina for a conversation that moves across all three chapters — leaving well, scaling well, and building for a generation whose expectations have shifted.

On succession:

• Why her board set a bar instead of hunting for a unicorn — and how that avoided the internal-candidate-versus-national-search trap that poisons so many processes
• The eight-month side-by-side onboarding and offboarding plan she built with her successor
• The outgoing leader's real last job: doing the hard, yucky things so the next CEO doesn't have to

On scale:

• What stays non-negotiable at every size, and what has to change
• Personalized learning plans for everyone — and why the "where do you see yourself" conversation should be bigger than someone's job
• Why engineering teams and teams of teachers have more in common than she expected, and why mission comes free in education but has to be built deliberately in a company

On what young people actually want:

• The two questions they ask first: what does it pay, and will this job still exist in ten years
• Why they're thinking about a good life, not a career — and Diane's invitation to leaders who find that framing uncomfortable
• Northeastern's co-ops, Minerva, and why apprenticeships still aren't a realistic pathway at scale

Find Futre at futre.me (yes, it's missing a vowel).

Transcript

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SPEAKER_01 0:01

Hi everyone, welcome to Higher Ground. Very excited to welcome my guest today, Diane Tavner. Diane co-founded Summit Public Schools. She started with one high school and grew a network across California and Washington. She also then handed the reins to her successor and is now the CEO of Future, a new platform helping young people figure out what comes next in their lives and careers. I'll let her talk more about that in a moment. Diane also chairs multiple boards and co-hosts the Class Disrupted podcast with Michael Horn. Diane, welcome. Thank you, Christina.

SPEAKER_00 0:33

It's really good to be here with you.

SPEAKER_01 0:36

Thanks for being here. So the first thing I wanted to ask you about is we talked to a lot of founders in our work as search leads and people that support boards. And one of the hardest things for them is actually making that decision to hand off what they've been leading to someone else. And it feels from what I've heard from the outside that you did that in a really thoughtful way that also was inclusive, but that felt very smooth and a very good transition. So can you talk more about your thinking around that and how you frame that transition in a way that was so positive?

SPEAKER_00 1:04

Sure. And it was, it was multiple years in the making. And so I think that's the first thing is that the the longer runway you can give yourself to think about a transition, I think, the better. It was long and complicated, but let me see if I can give a couple of the key points. So the first is that um I think it's a mindset of wanting to set up your successor for the greatest possible success. And I think sometimes founders are tired or they're burnt out or they just kind of want to get out. And so their orientation is not necessarily this responsibility to set up their successor for the greatest success. And I think that starts both with the selection process, identification and selection process, but then also in the transition and the onboarding and offboarding process. So, in terms of selection, I think one of the things we did really well was to convince our board that the next leader was in the organization. And that was true because we had done so many years of leadership development and exposure. And so the board really trusted the organization to surface the best candidates. And what the board did was set a bar for their expectation. And what this meant is that we didn't go through what I see very often, which is boards saying, well, I think we have an internal candidate, but we want to make sure that they measure up to any external candidates. And I think boards sometimes imagine these unicorn candidates that, you know, might be out there. And they end up doing this national search or this big giant search that really results in kind of hard, bad feelings inside and a lot of angst, and then not finding the unicorn candidate. And so um, I guess what I'm saying there is clearly defining what it is, you know, the the expectations and bar you have, and then recognizing that multiple candidates might meet that bar, and then you're really choosing among them was I think very helpful on our part. And and knowing that those, believing those people were internal and then not opening up to a giant search. And then the, I think the second piece was just deeply involving the organization in that process and really enabling the leaders who would be the team of the next, you know, CEO of Summit to be involved in that, engaged in that and invested in that. And we sort of normalized the idea of everyone becoming the CEO and gave them a chance to try it on and talk about it. So you didn't have sort of, you know, the sort of whispers and the behind the scenes and the factions that can develop sometimes in these processes. And then we gave ourselves plenty of time for trap for the onboarding and offboarding. So a full eight months where I worked side by side with my successor and we together built a plan for sort of on-ramping her and off-ramping me. And, you know, that that process of slowly gradually releasing and teaching and co-leading some things as we were going was really impactful and powerful. And then the last piece about that is I just committed to doing a couple really hard, yucky things that had to be done to try to clear the space to set her up. And I think as a leader leaving, that's maybe our greatest responsibility is to create the conditions for success for a new CEO.

SPEAKER_01 4:44

I really appreciate that. I know that's something a lot of interim leaders also try to do, which is what do we do to kind of make sure that things are clean for the next person coming in? Um, trying to get away from some of those really thorny decisions that can derail the first few months of leadership. Another thing that I always think with talent systems is as we scale and grow, and you know, you scaled and grew summit, you're scaling and growing a technology company now, that we need to understand what are those consistent non-negotiables that no matter what size we are and no matter what team we're on, people have to have and our systems have to be able to support. And what are things we need to change or update as we scale? What have you learned about that that you might not have known 20 plus years ago before you'd scaled?

SPEAKER_00 5:25

Yeah, it's such a good question. I think that I often find organizations, especially talent organizations, getting confused about who we are centering and what the purpose of our work is. And so as much as it's incredibly important to take care of our people and our adults and to develop them and support them, at the end of the day, I don't think we can ever lose sight of the we're we're here for the young people. And that is the purpose of our work. And constantly revisiting and making sure that what we're doing is on their behalf and in service to them, I think for me is a non-negotiable and is the most important North Star and grounding value that we can have as an organization. So that's number one for me. Um I think the second piece is I'm just a deep believer in continually developing and growing and that an organization is a learning organization. And so I'm very committed to everyone in the organization having a personalized learning plan at all times. And that doesn't mean that the company or the org is 100% responsible for that. I actually think that each individual is responsible for what they want to learn and how they want to develop and having agency around that. Um, but I do think you have to create an organization that cares about that, is focused on that, is providing real opportunity around that and is centering that as part of the conversation about what the employee is doing. Um, and just to make that very concrete, in every organization I lead, we're always having regular conversations about where do you see yourself in two years, five years, 10 years, and how can we support you in moving in that direction? And when I say where do you see yourself, it's a much more holistic question than just your particular job. Um, because I I do think that when you're developing people, you're developing whole human beings in their whole life. So um, those are a couple of the things that I think are critical.

SPEAKER_01 7:34

And how have there been any surprises going in from a traditional school organization where you'd spent so much of your career into more of a technology or they've been more similar than you might have thought?

SPEAKER_00 7:45

Um, I think people are people. And so in in many ways, very similar. In fact, uh I've started to notice some real similarities between engineering teams and teams of teachers, actually, and teachers and engineers. I think that that surprised me a little bit that they were so alike in in many ways and the lots of commonalities there. I do think that maybe in education we're a little bit more, for lack of a better word, touchy-feely, if you will, right, than I than I experienced with some of the other more business-oriented type teams. But people are people. And I also have learned that in education, we almost by nature are driven by impact and mission. Although I would say maybe some of my early jobs in districts were less connected to our mission. So there's almost like this built-in mission. And I think in a traditional company, you have to work a little bit harder if you want to be a mission-oriented company to really ensure that that's there because it's not necessarily naturally there.

SPEAKER_01 8:54

Some decisions you make are different, right? You know, being a mission-owned business myself, there are times where we make decisions where if we were just looking at the profit incentive, it might be different, and vice versa, right? If we were just looking at mission, it would be different. And that can be hard sometimes when people are coming in and out of different industries for them to understand those decisions in that frame.

SPEAKER_00 9:13

That's the certainly with the emerging generations entering the workforce. I think mission-oriented, whether it's a nonprofit or a for-profit, is much more important to them. I'm sure you see this. They're looking for mission-driven, mission-oriented workplaces. And so I think it's a huge advantage if that's who you are when you're trying to attract and retain talent.

SPEAKER_01 9:40

Both of us have young people who are either just starting or getting started into their thinking about their futures and their lives. And you created future because you really had the belief that the system wasn't doing enough to build agency and self-direction for young people at that stage. And so, what do you think employers need to hear from you or from people like you about what it's going to take to attract and support young people in those early parts of their career?

SPEAKER_00 10:06

Yeah, it's such a great question. I think that, you know, what we are hearing very clearly now from a significant number of young people that we're engaging with over and over and over again is they have a very holistic view of their life. And they really think about their future not only as a career and job, but about the people they'll spend time with and the other things they will do in their life and where they live and what that looks like. And I think that that sometimes gets represented in work-life balance or, you know, those types of terms. But I think of it more about just a healthy, holistic view of good life, if you will. And people are wanting to live a good life. And that is kind of a shift in some of the mindsets. If you look at kind of American history, I think it's a healthy shift. I think it's an exciting shift. I think it makes some people, my in my age group, uncomfortable to think about that. Um, we think about what we did and what we sacrificed and what we expected. And this feels kind of soft. Or I think my invitation is to everyone to explore and be open-minded and be curious about what's possible on that front. I'm hopeful that there really is a way that people can have good, healthy, happy lives and be really productive in their work that they're doing. And that that's a worthy pursuit for all of us of figuring that out.

SPEAKER_01 11:40

And there's so much fear right now around technology disruption, AI, what that's going to do for young folks in the workforce. A, are you hearing that from the young people you're engaging with? But B, what do you think we all can do about it?

SPEAKER_00 11:52

Yeah, it is by far one of the top two questions we hear from young people. The first question we hear is always about compensation and salary and they need to understand the finances. But the second immediate question is, is this job gonna exist? Is this career gonna exist in five years, 10 years? Am I wasting my time if I pursue this pathway because AI is just gonna take it? And there's a lot of worry, there's a lot of concern, there's actually a lot of anger about that among young people. And so they're trying to figure this out with very incomplete information. And I don't think anyone really knows exactly what's gonna happen, but they are wrestling with and trying to figure this out. They're also becoming very aware of the cost of college and post-secondary programs and return on investment. These are things they're starting to learn about and understand, and they don't want to waste time and money on degrees or pathways that are not gonna get them to where they want to go or not gonna persist. And so they're trying to be really thoughtful about that. Um, and they're worried about it for sure. I think the other thing is they're desperately wanting real world experience and experiential learning to better explore what it is that they want to do and are interested in. They recognize the limitations of sort of a class education that doesn't get them out in the real world and is really missing huge components of what's important. And so they are hoping for that, wanting that, and really struggling to find those opportunities and make the most of them. So I think there's significant possibility there for employers and education systems to collaborate to make this possible.

SPEAKER_01 13:43

Knowing you're someone that loves studying what's out in the field and a voracious reader and interested in so many things, are there good examples you've seen out there either on the higher ed space of folks that are being innovative or in this sort of entry-level worker support space that folks should know about that you think would be good examples of people to study?

SPEAKER_00 14:03

Yeah. I mean, sadly, there's not as much innovation on this front as I would hope there would be. Um, certainly there's a couple of uh great places to look though. Obviously, what Northeastern is doing with their co-ops is really interesting, you know, where young people are literally taking full semesters and going and working in the world and getting credit for that. I also, as you know, I chair the board of Minerva University. And I think this is a much more sort of integrated example of how the classwroom experience has been modernized in a way that makes it much more practical and much more engaging. These are the most engaging higher ed classrooms I've ever been in in my life. And their education is in the city that they are in, and it's designed to be very hands-on, project-based, and taking advantage of the real world in which they are in. So I would definitely study that model of higher ed. Um, and then, you know, everyone's excited about apprenticeships, and I am very excited about apprenticeships. Um, the challenge is there just aren't very many yet. And there's a lot of efforts underway to create more of them, but they're incredibly scarce at this point. And so not a super realistic pathway for most young people at scale. But clearly an apprenticeship well done is an ideal way to learn and grow.

SPEAKER_01 15:35

It's funny when you mentioned Northeastern. When Michael Horn and I were chatting, I said, you know, when I visited Northeastern with my son, I was so excited about it. He decided to go a different path for college, but I was excited about that co-op model. I thought it was really phenomenal. And I'm you I'm sure you've heard know a lot about this, but Gina Raimondo was talking about raise us and that work to kind of start to think about what it really means to have this transformation and what it's going to mean for young people and people of all ages. And so it is heartening. And I know you and I have friends involved in that effort. It's heartening to know that there are folks thinking about it. So well, before we wrap, what should folks know about your organization future? Um, and if they want to get involved, how can they?

SPEAKER_00 16:13

I think the thing to know about future is that it really is time for us to reinvent and modernize college and career readiness and counseling. Much of what we're doing in this space is incredibly outdated. You know, we're using these black box assessments from, you know, 70 plus years ago and tactics and approaches that are very transactional and not holistic and don't align with science that tells us about how young people are motivated and developed. And so future is very much about pushing us into this century and to thinking about how we truly help young people prepare for the life that they want, a whole life. And so we love the idea of working with anyone and everyone who's interested in that. Um, they can certainly, you know, find us on our website. Future is missing a second vowel. And so it's f-t-re-e.me. Beware of the autocorrect. But I would love for folks to reach out. There's all sorts of ways that we can connect and and partner if this is an area of interest for people. And we're excited to find find those points of connection.

SPEAKER_01 17:29

You've always been a leader in terms of thinking about where things are going for young people, where culture and talent and organizations are going. So thank you so much for your time. We appreciate your time, and I also appreciate all that you're doing in this area.

SPEAKER_00 17:41

Thank you.

SPEAKER_01 17:42

Thanks for having me. I appreciate it. Of course. Take care, thanks.