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Leading at high speed: empowerment vs. efficiency with CEO Danielle Diliberti

October 9, 2022 / 14:23 / E5

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In this episode, Danielle shares what she's learned as a first-time CEO about how to set people up for success, when to step in to fix something - and when to stay out of it, and her top strategy for building a culture of collaboration. Doing all this while building an industry-changing product is no mean feat, even without wearing three high-profile hats; but Danielle has a few tricks up her sleeve that you will want to steal - whether you are the CEO or you're just starting your career. These are strategies everyone can use to become a more effective team member and lead from within.


1:04 How Sommsation is disrupting the wine-tasting industry
1:43 Danielle's journey to CEO
3:08 How Danielle approached stepping into the CEO role
4:00 The "3/3/3" trick to quickly upskill people and teams
5:40 How to decide when to intervene, or challenge your team to do better
7:30 The golden rule for how much to expect from your people
8:12 When to NOT intervene
10:47 Strategy to build culture - while accelerating strategy, planning, and alignment

[00:00:56] Jasmin: Welcome back to People Changing Enterprises. I'm Jasmin Guthmann, and I hope you enjoy this episode with the Yield of the Birdie. You are the CEO of Sommsation. Tell us what the company does and how you came to be the CEO.

[00:01:12] Danielle: Sommsation is a modern technology platform or online marketplace focused around wine experiences. We're connecting consumers with world class wineries and top sommeliers. We designed the platform over the last year and a half to be really a user friendly, one stop shop with, direct access to a wide range of exceptional wineries that typically you can't find in the retail or, or traditional e-commerce space.

And so our team is trying to modernize what's a centuries old tradition. So I was part of the founding team that came up with the idea for Sommsation and I was first acting as CFO and COO in its infancy.

And it was really in about March of this year that we decided we were going to try to really accelerate the growth and development of the platform. So I stepped in as CEO, and really excited that we just launched our marketplace at the end of September. And now we're just kind of working on moving as fast as possible to bring great wine and experiences to the world.

[00:02:11] Jasmin: And how are you liking your CEO role so far?

[00:02:14] Danielle: So this is my first role as CEO, and not only are we a startup, but we're also a multi-sided platform and a multifaceted business. So it's very complex, but I'm really lucky we have a cross-disciplinary leadership team that really supports me in what I am doing.

So, you know, we are able to work together to bring the rest of the up the learning curves with our areas of expertise to do something really different. We are trying to change the industry and be a category creator, so we have very, very strong goals, and we're working a mile a minute to make it happen.

So that's challenging in its own right for me. There's just not enough time in the day. Knowing that I have a team and knowing that I can set my team up for success is really the goal as we build the business.

[00:03:03] Jasmin: And is that, it sounds a lot like you were leading by example. Was there a moment where you consciously said, Oh, now I'm the CEO. I need to do something differently.

[00:03:13] Danielle: For me it's always been about getting my hands dirty, knowing the goals of my team, and setting those goals for my organization. or earlier in my career it was understanding leadership's goals and I would always work towards that.

I found throughout my entire career that as long as I'm a really good team member, a lot of the leadership piece just kind of takes care of itself.

So for me, it's really about being a good team member, day in and day out, and making sure that I have strong conviction when I'm making decisions. Stepping into the role of CEO, my goal now is to make sure that I'm setting my team up for success and giving them the confidence to make those decisions.

So if it's something that I'm confident we already know how to do, I usually take a step back so that way my team can, you know, hone in on their skills. If it's something that I have experience in, one of the things I have is what I call the three, three, three rule, and I've used that throughout my entire career for myself and also for training my team. And so what that means is - you do it yourself three times. So if you are the person training after you've done it at least three times, and if it's a role that you've been in for a while, then you know you've done it, you know, probably 3000 times.

For a hyper growth company, you might have only done it three times, but once you have a little bit under your belt and you're trying to transition or train someone, then you have someone shadow you for three times and then you move to shadow them for three times and then you transition it off. So that gives everyone opportunity to continue to grow and to learn, but you have that knowledge transfer so that people aren't getting stuck doing the same thing if they don't want to be doing it. But also you're ensuring that you're setting everyone up for success. And so I deploy that tool all around.

[00:04:56] Jasmin: I wish someone would've told me that sooner. That's a fantastic way to really ensure continuous passing off the torch. And it also ensures that you don't just talk about the things that are important, but you actually have hands on experience. And during your Content Con 2022 keynote, you described a situation where, to me, it feels like that's a perfect embodiment. You challenged your teams.

You saw that the way they were using the CMS wasn't optimal and you intervened. And that was only possible because you had done it three times or 3000 to your point, and I'd love to know how you made that decision, how do you decide when you need to intervene and when you need to challenge your teams to do better?

And once you do, how do you actually do that.

[00:05:50] Danielle: Yeah, that's a great question and I wish I had the perfect answer for that because I think it is a continual learning curve. You know, it's so, I think there's a couple of things. The first, as I always think about - I want to ensure that I understand where they're coming from and what's going on.

Sometimes people are just have too much on their plate. Or other times people don't actually have the experience and aren't willing to say that. Having dialogue with the team and just getting people in the room to understand what creates a safe space. And sometimes that means being a little bit more patient and giving the business a little bit more time. And then other areas you can see that, you know, people are probably just slamming themselves into a brick wall. So some of it's just gut and experience. But really keeping a pulse on the organization to allow it to ebb and flow a little bit, but also knowing when to step in and telling people why you're stepping in, I think is really, really important as well, because it, it helps make sure that the human element is really there.

[00:06:55] Jasmin: And that probably then again, goes a long way in building trust, which is a prerequisite for telling you what the actual problem is. And I love the words that you chose earlier. You want to be the best possible team member. So you're being treated as an equal rather than the CEO that you know will get angry or mad, or that I don't want to share some things with because there's that weird level of hierarchy in between us. Would you second that?

[00:07:26] Danielle: Absolutely. Yeah. I mean, I think. I don't ask anyone to work harder than I'm willing to work myself, you know? So I, I think that that's one of the golden rules. I travel a lot and I, I spend time on each of the coasts in the states and, and then also I'm, I'm in Europe and London quite frequently, so, you know, my team knows that when I'm on the West Coast, I'm going to be up at 5:00 AM with coffee in my hand and I'll be working right alongside and I wouldn't expect anyone else to be doing that if I wasn't willing to do it myself. So I think it's really important to make sure that as a leader, you're always looking in a mirror and making sure that you would like your employees or your team members to do what you're doing. Because if you're not, you know, it's something you need to think through.

And then I would say that the one other thing for me is, It's a challenge to sometimes take my hands off, right? Because if I know I can do it quicker in the short run, then you just want to do it yourself. That's just inherently what people do.

You're like, I'll just take care of it and we'll be done with it. But you know, one of the things I've learned is you really need to invest the time and the attention. And to your junior employees or people that want to shift gears to help them get up those learning curves, because as we talked about earlier, passing the torch really does help everyone.

And then the whole team gets smarter, the business becomes more valuable, you can move a lot faster. And so that investment upfront will really pay dividends in the long run. Even when you just want to get it done yourself. So that's been a learning curve for me and, and a growth opportunity for me as a leader is to say, Okay, I know I could do it 10 times faster than someone else, but.

If I do the 3 33, then we'll all be able to do it faster in a very short amount of

[00:09:08] Jasmin: time. Does your team hold you accountable to that?

[00:09:13] Danielle: They do. Yes. My team is constantly bringing me new ideas. They're asking for more. Or they're sharing when they, you know, are, are doing something that they think is not aligned with their skill set or what their goals are.

And so I think, you know, that creates great dialogue and I'm constantly reworking my org chart. Um, you know, I think I hired five people in the last month with Sommsation and we just talked to one of our recruiters and we have another five job specs going out. And some of those roles are replacing.

Things that people are doing because they want to move into something else and so I try to make that happen every chance I can. And then some of it is just a huge growth opportunity.

[00:09:53] Jasmin: That's amazing. And I think that is the key to empower people really, because if you want to pursue that growth opportunity, it is about not settling for what the status quo tells you would be, right.

Or the thing to do. But it's actually looking at the data and. Adding your gut feeling and then coming up with new solutions, with new ways of doing things, challenge yourselves and everyone else on a team to do better and be more creative. Is there anything from a culture perspective that you can do to propel that even further from your point of view?

[00:10:33] Danielle: Culture is something that I'm constantly thinking about ensuring. That you're creating a dynamic culture, ensuring that DEI is top of mind, but then also having a culture that exists and that, you know, it has some tangibility to it, is also important, especially in a hybrid world or a fully remote work environment.

For some, finding that culture has been a challenge. One of the things that we do at Sommsation is summits, very discipline dedicated summits. So we have data and analytics summits. We have engineering summits, sales and marketing summits. We're getting ready to ramp up an operational summit. That's gonna be three days, and we think it should be two weeks, but it's getting all of the right people in one place and dedicating 2, 3, 4 days to making sure that everyone's aligned, to making sure that we have a roadmap in place. From a strategic perspective, you typically have a roadmap. You might have a technology roadmap, but having an operating roadmap and a marketing roadmap and ensuring that those are all aligned and then spending dedicated time on them has been a huge value for our culture.

Because if you get marketing and creative team members in the room, and operators in the room, and the accountants in the room, and you're talking about all of those different disciplines at once. It's really hard to align everyone versus when you step into the room and know that you're talking about marketing. The accountant can take off their accountant hat and think about it from a marketing lens. So that creates, you know, not only some continuity between different business groups, but I've also seen that it really helps the culture because people can connect in a different way. And so then for those teams that are hybrid or remote, having that extra connection or even one or two of those aha moments really do help build your culture. So that's one of the things that's really, really important to me and that I'm spending a lot of time on right now in an early stage company because I've seen if I take my foot off the gas there, it can go awry very, very fast.

[00:12:42] Jasmin: because people have such a tendency to stay within their own known space, right?

The accountants stay with the accountants, the marketing people hang out with the marketing folks. But what I've seen many times is once you have them together in one room and they learn what the others are doing, there's a lot of aha moments. Purely because people weren't aware of what the other people were doing.

[00:13:09] Danielle: Exactly, exactly. And investing that time is a challenge. You know, trying to get the marketing team to focus on operational workflows and, and understanding how things are entering our data warehouse or being pushed out to our content management system. You know, that's not top of mind for. But it actually really improves the way they work in the long run because they recognize if I, you know, adjust X, Y, and Z, I'm gonna help my team members become a little bit more efficient.

Or, you know, it's one less touchpoint that we need to think through because now I understand how it works, you know? So it really gives different working groups the opportunity to work better together in the long run. But it's an investment. It requires time and effort. And when you're investing time and effort in one thing, then you know that's an opportunity cost somewhere else, and leaders need to be thinking through that pretty regularly.

[00:14:08] Jasmin: Thanks for listening to People Changing Enterprises. We'll be back next week with a new episode, helping you make your mark.

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