Cloudflare TV

Leading with Talent: Playing the Long Game

Presented by Melissa Daimler, Scott Tomtania
Originally aired on 

Leading with Talent: Playing the long game" is a weekly show on Cloudflare TV that highlights amazing talent & people leaders in tech. The purpose is to amplify the stories of incredible talent & people leaders showing up every day building companies impacting millions of people around the world.

Today's guest, Melissa Daimler, has been an executive at high-growth companies for over twenty years. She is now the Founding Principal of Daimler Partners, working as an advisor, facilitator, and executive coach. Her primary focus is helping leaders design and operationalize culture.

Her experience as an executive and now as a consultant includes coaching executives, helping teams work more effectively, and building scale-proof organizational processes & practices.

Melissa has served as a board member for the Association of Talent Development (“ATD”) and the Advisory Board for the University of San Francisco, Master’s Program for Organization Development. She currently advises One of the first coaches certified by the International Coach Federation (“ICF”), Melissa graduated from the Pepperdine University Graziadio Business School with an M.S. in Organizational Development.


Transcript (Beta)

Hi everyone. Welcome to our second episode of Leading with Talent and Playing the Long Game.

Today we have a very special guest here whom I've worked with in the past and I've admired.

We have Melissa Daimler, the founding principal of Daimler Partners and she's been an executive for well over 20 plus years and she's currently a contributor to the Harvard Business Review and Forbes.

I will steal your thunder Melissa.

I know we go a little bit back so I'll let you introduce yourself.

Great. Well Scott it's great to be here. Always good to talk with you in whatever forum we have.

So thanks for that introduction. Yeah so I've been in tech for after 20 years you just say 20 plus and you and I got to meet at Twitter and I didn't realize but we actually were there at roughly the same time for almost four and a half years and what I call the glory years.

It was a just a great time to be part of the company.

Just a lot of high growth. I think when we started it was under a thousand employees and when we left it was around 4,500.

Exactly. A lot of people weren't part of that.

I remember close to 700 or so, 6-700 when I started in the old AT&T building and then we moved over to the building on Market Streets and then yes I clearly remember that and I clearly remember you sort of leading a lot of the foundation work for our learning and development philosophy and then many more.

So super excited to chat a bit today. So I want to learn more about your journey overall.

So part of this conversation is to understand how you started from the very beginning and how you ended up where you are today and what sort of ties all of it together.

Sure. So yeah I'll give you the two-minute or three -minute version.

So I was in New York City for a while after college doing training programs and actually was part of one of the first coaching organizations, one of the first certified coaches before a lot of people around the world became coaches.

I started teaching coaching so just that's when I started doing a lot of executive coaching and working with both teams and individuals and then the dot-com bubble happened and my husband and I really wanted to take advantage of that and kind of figure out what was going on over here.

So we moved across country and I worked for a company, a startup and before this title was even around was the director of people and was just coaching the executive team but then that turned into leading HR and so got a lot of good experience for a couple years there.

I would say a couple themes are in my career.

One is there's no job that I've taken that has been the exact job description.

So everyone and you're familiar with this too, I mean you co-create, you figure out kind of this is good but I'd like to do this as well and I did that with the Adobe opportunity.

So there was an opportunity to come in and be an HR generalist and also launch a coaching initiative and kind of get coaching throughout that organization.

So I worked at Adobe for quite some time, almost 11 years which seems unheard of now but got to do a lot of different things.

High growth company as well, 3,000 employees, 12,000 global, two major acquisitions, moved our business model into the cloud from shrink wrap in boxes.

So just a lot of good experience in learning the business as well as understanding kind of all the different parts of people in the HR function and then of course, Twitter called and you take the call from Twitter and Janet and that was even something that we co -created.

So we evolved that role a bit more and as you said, was able to kind of start something from nothing and build that over time and learned a ton.

So just a lot of good experience with companies that cared about culture, cared about values and the other theme I would say beyond just being a builder and kind of co -creating my jobs was the idea of kind of systems thinking and looking at things more holistically.

So at Adobe, we had some really good values, we iterated on those a few times and embedded those behaviors into all of our processes and practices.

So really got interested in making sure that we were always looking at what our strategy was and how we were working and the same for Twitter.

So the opportunity to kind of see what it looks like when that isn't valued as much, we work was I can say now a good opportunity for me.

I don't think leadership was as invested in and I think the values on the walls weren't necessarily things that you were seeing on an everyday basis.

And so after that got really interested in making sure that people work in companies that have cultures that feel safe, that feel engaging and where you can be learning all the time.

So that's the work. This is so fascinating how you sort of summarize everything and you talk about what you've learned on your journey.

You used two words that really stand out to me, co -creating and also systems thinking.

And I know you've worked with a number of iconic leaders very closely such as Dick Costolo, the former CEO of Twitter, Donna Morris at Walmart, Janet Van Hise, my current boss.

So how did you sort of come up with those two terminologies?

Because they're really ingrained in your entire journey and the stories that you're telling around HR currently and your philosophy and what you're sort of building.

Yeah. You're a learner too.

I'm always learning. I'm always trying to figure out how to get a little bit better.

I think Donna, the big piece that I learned at Adobe and particularly with Donna was to always keep, and you and I've had these conversations as well, the business in mind first.

So it's understanding the business strategy.

And I tell the story when I first met Donna, it was through an acquisition and we were all getting ready to meet her and hear the whole kind of how the HR function was structured and learn a little bit more about the people.

And so she was coming in and she just launched into, let me tell you about the business.

Here's our customers, here's our strategy, here's our challenges.

We barely got to the HR part.

And so it was just such a great learning and just a reinforcement that we are in the people business and that has to be integrated into how we're thinking about the business strategy and for you all the time, working with your hiring managers and understanding what their needs are and potentially what they don't even know their needs are.

What's around the corner for us? How are we continuing to look forward?

So that was a huge learning. I think Janet, I learned, of course, so much from.

I think the biggest piece there that I continued to learn that she modeled was just use your team.

She empowered her team. She had your back.

She even said, I may not know all the details, but I hired you because you're an expert in this area.

And again, I will support you and empower you, but she really leverages her team and expects a point of view and recommendations to be put forth.

This was one of my lessons that I was going to share later, but I'll share it now.

Great, let's do that. One of the lessons from Dick was the idea of, and I think we're continuing to learn this, but having more space in your days.

And I remember him saying that he would be in his office and just looking at his whiteboard or not necessarily on email or on a call.

And he said, if we just do back -to-back meetings, we're never going to have time to do the real work.

And so I really took that lesson and I work a lot with executives now in just, how are you designing your days so that it's not just meetings and emails, but it's, we want your thinking.

We want you to have some time to be able to craft what our next strategy is.

That's such a practical advice. I think you touched on, Dawn, I touched on Janet having your back and supporting, and then you touched on Dick Costolo, actually one of the business CEOs at the time that I knew with the high growth of Twitter, talking about space, creating space.

And sometimes we think we're too busy and we can't do that, but not having that space really could lead to other dangers, right?

Not being able to really fully execute or be able to show up as the best people leaders that we want to show up.

Don't you think so? Exactly. Great.

So switching gears, really the topic here is playing the long game. And you and I have discussed this briefly.

And one of the main reasons why I wanted to discuss this with a number of real talent leaders and people leaders is that sometimes we can be very short-sighted in our approach, right?

We're thinking business, we're thinking people.

We want to build a very diverse team. We want to make sure that we help the companies elevate themselves.

But when it really gets down to the execution piece, we sometimes really do things that are very short-sighted.

So what does playing the long game mean for you, Melissa? Yeah, I love that question and I love that this is the title of this podcast.

I do think it's what you said.

I mean, I do think it's a combination of being able to be strategic, kind of look around the corner and look what's ahead and have time to be thinking about that with your team and also be scrappy and execution-oriented.

So I, but again, having time to do both.

And I think a big lesson that we learned last year is being able to pivot quickly is really important, but you have to first know what you're pivoting from and what you're pivoting to.

So, you know, ideally you already had a strategy in place, people kind of knew what they were doing and how they were going to do it.

But short term, we had to figure out how are we going to change things?

Customers that we thought we were going to have aren't happening anymore.

Revenue isn't what it is. So I think playing the long game is always being clear about what your long-term strategy is and also knowing what your next step is.

I used to ask my team all the time, we would be in meetings and you know, at the end we would say, what is the next step or what's the action out of this?

And I just think so often we don't close those loops. You know, we just, we run from meeting to meeting and, you know, we're not really clear.

Like I remember that meeting in the morning, but what was I supposed to do and who was supposed to be what?

And so I just think clarity is the word I think of when I think of the long game, you know, like just being really clear about that long-term piece as well as what's right in front of you for yourself, as well as your team.

Yeah, that's, I think that really stands out there.

So playing the long game, being clear about your strategy and inevitably, even if you're doing both well, you're going to make some mistakes, right?

And you know, I've made plenty of mistakes. I continue to make mistakes and I'm learning from them.

Yeah. Can you touch on some of the mistakes and learnings that you gathered through your journey and what you want to share with us?

Yeah, I know. And when we talked about prepping for this, I said, there's too many.

You know, that actually tied to this topic. You know, when I first started managing, I think, you know, I was trying to either be, I got feedback that I was too much of a micromanager.

I was too much in the details.

I was asking too many questions. I wasn't trusting my team. And so I went to the other extreme and was almost too strategic, like too high level, not knowing all the details.

And so I was struggling between these two extremes versus one of my mentors at some point just said, look, it's not one or the other.

It's, you have to dance through like, and there may be some people on your team that you have to be, you know, a little bit more tactical with.

Maybe they're new or maybe they have skills that were still, they're still developing.

There may be some people on your team where, you know, you do need to talk strategy with them a little bit more.

So I think this idea of, you know, what I, what I call polarity thinking, you know not me.

I mean, it's that, that idea has been out there for years, but you have these two extremes.

And I think so often we operate in this extreme way.

We think we have to go from one extreme to another versus, and I mean, last year I talked with so many executives who were trying to figure out, you know, should I be empathetic or should I just be focused on execution, you know, execution oriented or empathetic?

And it was, yes, both. And so this, this, this idea of, you know, kind of learning from my mistake of trying to be one or the other versus, you know, depending on what the team needs at the time or what a particular team member needs specifically, how do you kind of move between those, those places?

So not being too micromanager or not being too high level. I think another learning was just, you know, as a, again, from a new manager standpoint, and even as a colleague, I think I always had to have the answers initially.

And then I had to look like I was the expert and I knew what I was doing.

And instead of, you know, asking good questions and really listening and, and kind of, you know, you like that, that word co-creation.

Yes, I do. Because you are a co-creator.

And so I think that's really important to remember that. And again, last year we, that was reinforced.

It was a forcing function to say, and even now we don't know what hybrid workplace is going to look like.

We don't know where this is going to go.

And so continuing to be in touch with your employee, employees and colleagues and, and asking good questions instead of always feeling like you have to have the answer.

I think a good one. The last one, you know, I would say I made the mistake and all of the companies I worked within to kind of drop what I'll call my personal foundation, you know, just health is one of my values and, you know, working out in the morning, meditating, um, you know, eating healthy is, is really important to me.

And, you know, my, my team used to know when I didn't work out, I didn't meditate because it definitely showed up in those meetings.

So I just think, um, it's so important to manage your own health and wellbeing, you know, your physical and mental wellbeing.

And, um, you know, again, we, we were, that was over the last year.

You've just talked about your own physical health, mental health and wellbeing.

I love that piece of it. Another, uh, part of it, which you really know about me is that I, I, uh, I like drumming.

I'm a, um, I'm a drummer and I also love sports.

Um, and I draw from those two poles that bring them together, right.

At the end of the day, it feels like a people's strategy is a business strategy.

A people's strategy is also about us and where we draw from. And, um, I'm going to pick on you here a bit.

I, you are a design, you are a design person.

You are into, uh, some of the best designers out there and it shows up in your people's strategy and your work and how you think about talent.

So why don't you share a little bit with us on that?

Well, that design is one of my values too. Um, I think, and to your great point, I mean, I think it shows up in a lot of different ways.

I mean, I think how from, you know, everything that we shared at Twitter, you know, kind of our, our branding to how we design learning experiences, um, how we design, um, right now there had to be a much more intentional design when we came together with groups last year.

And now on, on zoom, you know, it's a different, it's a different kind of connection.

So how do you, how do you design for, um, connection instead of just always designing for, um, outcomes?

And I think both again are important, but so many people are craving connection.

And so I've done, you know, kind of more breakout rooms than I ever have in this last year and up create, created and designed opportunities for people to, um, to just check in with each other and, um, see how they're doing.

So, um, and design, I think of things too, like I'm a writer, you know, I love writing.

Um, I love speaking. You know, I, I think there's so many, um, ways that you can design your life and, and I love your expression of, of drumming, um, that you're continuing to incorporate that.

I think that's really important. That's great.

Great. Great. Now, um, with your journey, you've just shared a lot about your, uh, some of your mistakes and your thought process, co-creation systems, thinking, designing, uh, what sort of advice would you give to these three separate groups?

Um, I And then three, even recruiters, if you just want to address any of those segments or you just want to, you know, you have advice for, um, lots of other segments out there.

Yeah. I mean, I think this summarizes some of what we've talked about.

I mean, I think, um, I'm working with a lot of CHROs right now and, and heads of talent and recruiting.

And again, nobody kind of knows We're all, we're trying to design this thing in a way that, um, is fair.

People feel safe. Um, they're, they're taking into consideration their employees perspective.

I think, um, that's something to always remember.

I, um, talked to somebody a few weeks back, an employee who was at a company and they sent out a survey on, you know, kind of what your preferences are, never followed up with the employees on the feedback, and then just announced some of the policies that were going to happen, but I'm not sure if they took into consideration the survey input, but, um, you know, that, that was a miss.

So I, I think if you're asking your employees for feedback and you're doing surveys and you're having different communication forums, incorporate that and take that, that doesn't mean that you have to have consensus and you have to do what everybody wants to do, but acknowledging that, you know, we heard you and this is the decision we're making.

And again, just being really clear and know that we're probably going to iterate, you know, three months, we're probably going to change this thing again.

So just being continuing, we've had to be continuing to be flexible and agile as we're, we're figuring all this out and staying as close as possible to your employees.

I think from a, um, a recruiting perspective, I'd love to hear your thoughts here, but just, you know, sharing how you coped last year, you know, what, what were some of the stories, the war stories on the front line from the company, you know, what did you learn that was surprising about how the company was able to pivot?

How, you know, how the employees come together?

What are the personal stories that, that you heard, that, you know, kind of show the values of, of the company?

Um, so I think those would be some of my pieces of advice.

I mean, I, I work a lot with companies right now around designing intentional cultures.

So I think intention is a big word right now and being intentional in, you know, kind of that playbook of how we work.

So, you know, what are your behaviors?

What are your processes? What are your practices?

And with teams, I'm, I'm working a lot now around, you know, we're, we're resetting on all of those practices that, that you and I know and love, you know, how are we, how are we doing with our meetings?

How are we doing with decision making?

How are we doing with constructive debate? Um, and because again, it's just a different, it's a different time and we're still kind of zooming in here.

So, um, continuing to kind of iterate and revisiting those practices, I think is a really important thing, just checking in with individuals and teams.

You've touched on something around the need for more communication is something that employees have gotten used to during this pandemic.

And it's something that should be applied, um, across the board.

Um, how do you think, um, I know here we're sort of extrapolating right now and dreaming about what this could look like.

What, what do you think, uh, two to three years are going to look like if you were to, um, you know, see all the trends sort of play out?


Oh my God. Um, I, you know, it's so hard to predict, but I, I mean, the trend right now where we're going is this hybrid workforce.

So how do we, we still want to see each other, but again, we want to be more intentional about how and where we do that.

So maybe it's two or three days in the office and then two or three days at home.

Um, and so I think we're going to see that. I think the challenges are making sure that everybody does have exposure, you know, whether you're in the office or not, because we don't want to go backwards with, you know, all of our diversity efforts and the flexibility efforts that we had, uh, with parents and people, you know, caretakers and people who may not have the option to come back into the office.

So how do we make sure that as we're thinking about all of this, that we're, we're thinking also about inclusion.

So, um, I do think there's going to be, I don't think we're ever going to go back into the office five days a week.

I think there's going to be a hybrid and I think the office space is going to change.

I think we've been talking about this for years, but now I think we're finally going to have more collaborative spaces, places where people can, you know, really connect and have those kinds of conversations that may not work as well.

Yeah. Yeah. I think so from a recruitment point of view, I think some of the efficiencies that we've gained, uh, with being able to schedule candidates without having to fly them everywhere, necessarily those are going to remain.

Um, I think that we have found ways to really speak to each other, um, through a video conversation, uh, clearly we found ways to empathize.

We've found ways to be inclusive.

Um, it used to be that you had to do all those things in person, right. Yeah.

To be even more effective. So from a recruiting perspective, that's what I see that will remain.

My, um, other question for you is, uh, how does this all feeding to sort of like the, uh, learning and development space, right.

What are we going to do to be able to get ready for the shifts and with the sort of, uh, skills and, um, opportunities that the next level of talent is looking for with the hybrid situation?

What are some of your thoughts? Yeah, that's, that's a good one too.

Um, I think, you know, just like what you've experienced with recruiting, we've experienced that as well from a learning perspective.

I think I've always believed in this, um, idea of, of learning communities and learning cohorts.

I think that's, that's the best way to learn, you know, instead of, um, you know, kind of going into a classroom for, for two days, we realized that I'm a terrible student with that.

Like, so it's just hard to take in all of that information, um, versus having kind of a cohort of, you know, seven to 10 people who are in similar situations.

Maybe they all just got promoted to director or senior manager. Um, but they want to learn, they want to learn something new.

They want to talk about it with each other and they want to practice coaching in a safe place.

And so over this past year, I think, um, I've been doing that more over Zoom where communities are coming together and we've been able to use, like I said, the breakout rooms and, um, you know, over a period of time, you know, six to eight weeks.

And so I think, um, we're going to continue to do that. I think it's, it's similar to what we experienced 10 years ago in blended learning.

You know, people still want to come together for those key milestone, uh, events, whether it's a launch or ending or, um, someplace in between, but I think for learning and, uh, connecting, uh, Zoom is going to continue to work well.

In terms of skills. I mean, that's a whole nother session, but I do think, um, you know, the emphasis on, I feel like the manager still has the hardest role.

I always believed that that, that is kind of a linchpin role of every company and it's why we spent and invested so much Twitter.

It was called Twitter core five. Just, you know, when the manager this last year, they've been not only doing all of the responsibilities of a manager, but also being a counselor and, um, a psychologist, you know, just, you know, really trying to be, um, going back to that empathetic and executor, um, really trying to be there and, and, um, be in that person's shoes, if you will, and also make sure that they were clear on what the goals and objectives are and what help they needed along the way.

So I think continuing to focus on managers and, and making sure that they have the skills they need, um, to connect with people and to get, get the work done, I think is, is really important.

This is great. Great. Great.

So if I'm hearing you correctly, um, essentially with your journey, uh, some of the things that summarize for us will be mixed empathy with execution and do it well as a, as a, as a manager.

Correct. Yeah. Yeah. I think, um, being able to, you know, going back to those coaching skills, like being able to empathy is, is listening and, um, asking good questions and not always be so focused on, um, you know, a lot of one-on -ones over this past year, as you know, haven't been about the goals of the company.

It's been just a, how are you really kind of conversation.

And so I think continuing to, to make sure that, that, um, like that, that continues.

I mean, I think that's part of any kind of good manager employee relationship, whether or not we're in a crisis.

That's great.

That is really, really great. Well, thank you very much, Melissa, for joining me on the segment.

I know you're extremely well sought after, but this is, thank you so much.

And thank you. Great. Thanks, Scott.