Lead Lead, and Not Lead Follow (Zendesk) | Datadog

Lead Lead, and not Lead Follow (Zendesk)

Published: July 17, 2019


Well, my name is Blake, and I’m the Director of Site Reliability Engineering at Zendesk.

I’ve been there for a little over a year and a half now and I was hired to build a reliability organization from scratch.

I previously held leadership positions at Netflix, Blackboard, and an agency called SolutionSet.

Yeah, this is kind of bright. Oh, yeah. By the way, I’m not perfect.

My slides contain only words, no fun pictures or GIFs. Sorry about that.

Here’s an overview of what we’re going to cover today.

First, I’m going to describe what I mean by Lead Lead. It’s important that you understand the team approach I’m talking about today.

Second, I’ll cover the role of leadership and management within this type of organization and approach.

Third, I’ll talk about how we’re building and fostering a team culture to support this approach.

Then, I’ll talk about how my organization fits into the company-wide processes when it comes to planning, prioritizing, and aligning with the rest of the business.

Last, I’ll review and touch on some of the benefits of this Lead Lead approach.

So let’s get started.

Unpacking the concept of “Lead Lead”

So, let me spend a little time going over what I mean by Lead Lead.

I’ll also provide a couple real-world examples and experiences that I’ve had when applying this approach.

Lead Lead is when everyone on a team feels safe and empowered to step up and do what’s right for the company, find a problem, propose a solution, and get it done.

The other day, I was having a one-on-one with an engineer on my team and I could tell something was on his mind.

So, I flat out said, “Hey, it looks like something’s on your mind. What’s up? Something bothering you?”

He jumped right into stating how we’ve had some poor performing queries that have started backing up connections and could possibly lead to an incident if it hasn’t already.

He then asked me, “What do you want me to do?”

To which I replied, “Well, you tell me what we need to be doing here.”

After a pause, he said, “Hmm, if I can pinpoint that piece of code that leads to these queries, maybe we can put some guard rails in place to prevent this from happening.”

To which I applied, “Sounds like a great idea. Are you able to pinpoint that now with our current observability?”

By the way, I’m paraphrasing here, this isn’t word for word. I don’t have a Slack conversation or something to pull it up here.

He pretty much said, “We can’t” for some valid technical reasons. But he had an idea of what to do to improve and bring that observability to the surface.

He proposed a pretty solid approach, but that still didn’t stop me from bringing some probing questions, trying to poke holes in it. It never hurts, and it gets people to really think outside the box and zoom back a little bit from when they’re deep in the weeds.

So then, we talked about it and we’ve talked about how we should prioritize this work against the current work that he’s undertaking.

Don’t want to overload him. So, if he’s gonna take on new work, we need to move work off his plate.

So we talked about some of the work that he was doing, and some of the impact he thought that was bringing the value, and then we did some…and then we talked about how this can provide value to the company.

And we ended up both landing on, “Hey, okay, this sounds like a high priority. Let’s move some of your other tasks off, whether the team can help out, or whether it’s put in the backlog, let’s do that, focus on this.”

So, he was off to the races after that.

He got it implemented, was being used, and then, we got some great praises from other teams because they were using this often. They were able to prevent incidents from happening by seeing where these queries were coming from.

So, this is again an example of when someone feels safe and empowered to just step up when they know something that’s good for the company.

Including your team in prioritizing tasks and sketching out roadmaps

Lead Lead is when the whole team has input on the roadmap and priorities.

I touched on prioritization a little bit in my previous story, but I also want to talk about how I’m a big fan with the whole team taking part in producing a roadmap.

That way, it’s more realistic.

I don’t have necessarily the pulse on some of the problems we’re gonna need to solve and some of the hurdles we’re going to run into.

They’re really working within this code base and within these systems day-to-day, so they know best. Plus they’re the ones doing the work. Shouldn’t they have a say when what we’re working on and how long it should take us?

So anyways, those are some of the values that I see by bringing the team into these discussions, working together to put together a roadmap that we can all get behind.

I plan to have an offsite with my team later this year so we can go into 2020 planning and do it together as a team.

I’ll later cover how we do quarterly planning and how the team’s involved in that as well. It’s not just me doing the planning and saying, “This is for you to work on.”

Encourage difficult conversations with anyone

Lead Lead is when folks are encouraged to bring up tough topics that benefit the company with anyone in the company, no matter what their title is.

I have someone on my team that recently met with the senior VP. Prior to the meeting, I asked if they were planning to bring up a pretty big and potentially tough topic regarding error budgets.

My intention wasn’t to stop them, but more to encourage them as I know that this has been on their mind quite a bit, and they have some really good, valid points that I think needed to be heard throughout upper management.

They ended up talking it out or talking about it with our senior VP. They had a great conversation and ended up being totally aligned.

It was so powerful to see the positive reaction from the conversation as they shared it with me that later on in the day, and then even a couple days later, when they brought it to our team meeting and they shared it with the team.

It was so infectious, the positiveness, that the rest of the team was just rallied behind it. It was beautiful. It’s beautiful.

The what and the why

Lead Lead is when people are informed of the what and the why. Then they get to decide on the when and the how.

A couple of jobs back, we were actively pivoting our Box Enterprise software that runs on-prem to a SaaS offering running in the public cloud.

I’m sure you could imagine this brought a lot of interesting technical challenges.

One of the most challenging things that we were hit with right away, especially from a scaling standpoint, is, there are these plugins that you would install. And typically when you’re running on-prem, you have administrators that run the software and they can go into the admin panel and upload plugins and install them.

Well, for us to be able to run a somewhat contained SaaS environment, we were the ones that were controlling the plugins and then they would go in and enable and disable. So, we had to actually do the uploading and installation of plugins. This was a totally different approach than we’ve ever had to solve.

So, I met with the product folks to understand, what’s the volume we’re gonna have to deal with?

Like are we talking like 10 plugins and that’s it? Are we talking 100 plugins and then we’re gonna have 100 more the next day?

So, I really started gathering that context on what needed to be solved.

And then, I wanted to understand the why.

So, I started asking folks in product and other folks in our success department, “Why is this such a critical thing that we invest time in and that we get to a place where we can install these to keep up with the velocity that we need to?”

That’s when we were told that it was pretty critical to everyone’s workflow, and there were definitely some standard plugins and an ongoing marketplace that we’re gonna need to adapt to and be able to provide in order for customers to move off of the Box Software to the SaaS offering. This would be one of the blockers for them.

So I gathered all that context up.

I brought it to my team and we sat down, we talked it through. I said, “Okay, now that you have the what and the why, tell me about the when and the how.”

Then, it was great. Team just started collaborating, started whiteboarding, started coming up with some possible solutions, talking about the complexity of it.

Do they want to invest in something that’s short term or something that’s long term?

Do they want to invest in their owning it, or do they want to invest in a self-service tool?

What they ended up landing on was, they ended up developing an upload tool, an installation tool, that worked with our SaaS offering.

And they decided to do it right away because they saw that it was critical in order to get people to adopt the thing that we were building.

So they got together, they put together the plan and they executed. It’s still being used to this day, by the way.

What role does leadership play?

Okay. So, let’s talk about the role of leadership with this approach. Leadership and management.

What are the things they should be doing?

Get out of the way.

Well, I’m kidding…kind of.

In my opinion, there are four things a manager needs to do in a Lead Lead environment. Let’s go over them now.

There are other things as well, but I’m going to touch on some of the four major ones, I feel in my opinion.

Bring in top talent

Recruiting and hiring top talent.

And to be clear, top talent doesn’t mean some Super Ninja, 10 times engineer from an Ivy League school.

Top talent is someone you’ve interviewed and think will be great for the team and the company.

It takes a lot of work to get to that point. That requires putting together and running a hiring process that provides a good candidate experience and treats them all fairly.

Countless hours of finding diverse pools to source from and just sourcing from all the other different pools out there, building up a good pipeline, keeping in contact with folks in your pipeline so when they become available, they think of you.

Going through the interview process, and taking up other people’s time. So, you want to make sure that the interview process is well planned out and efficient.

Then, you hire them, but it doesn’t stop there.

Yes, hiring top talent can be a full-time job, especially in a competitive market that we’re in and when we’re trying to scale an organization quickly.

By the way, we’re hiring.

Keep top talent at your organization

Next up, retaining top talent.

You’ve hired them. It’s great you’ve hired them, you’ve got them in the door, you’ve got them sitting in the desk. Now what?

I tell you what, keep them happy and engaged. You wanna set up new hires to be successful once they join.

At Zendesk, we use welcome letters that outlines a few things to get them started.

It covers things like how they’ll impact the team and company. It introduces them to the team. It provides them with other contexts they can leverage throughout the organization as they’re ramping up.

It provides them resources and assigns a buddy they can partner with as they’re onboarding. It lays out what they’ll work on first, as they get to know the company better and can identify what problem spaces they need to go work on and solve.

Ensure the team is working on impactful projects, and providing value to the company.

I know I’m motivated when I’m working on impactful stuff.

Give them challenging work, so they can continue to grow. Without challenges, work can get boring, and engagement will decrease.

Speaking of growing, work with individuals on your team to help career growth, put together a development plan to keep them moving along their career path.

This gives them clear direction on what they need to achieve in order to move up in their career.

Providing actionable feedback is also extremely valuable to an individual’s growth.

Feedback should come from a place of caring with a goal of improving one’s performance at work.

Listen to your reports and act on what you’re hearing.

Sometimes they’re not gonna have all the time and energy to solve all the company’s problems. And they shouldn’t. That’s just not fair.

Sometimes you will need to be the one that steps up on their behalf, and add volume and energy to their voice.

Empower them to do what’s best for the company and you’ll more than likely have happy people that want to stick around.

Some of the things I’ll talk about later regarding team culture also helps retain talent.

Be a conduit for communication

The third area of focus, providing context and communication to your team and folks outside of your team.

The amount of context can be overwhelming, especially as a company rapidly grows. Your goal is to distill all of the contexts swirling around the company and inform your team on what matters in their day-to-day.

Collect info from other groups and bring back the important bits to your team. Absorb all the memos, and inform your team what’s going on.

Sometimes, you might actually ask your team to read a memo because it’s so good and it’s so impactful that they should just read it instead of you trying to condense it down and delivering it.

Attend informative meetings on your team’s behalf and bring back what you learn.

This keeps them from being distracted by meetings and able to focus on the work that they’re doing.

Go out and ask for feedback on your team. Gather that feedback and bring it back to your team. It’s always good to hear how your team is perceived throughout the organization because there might be key learnings that your team wants to learn from and apply those lessons to improve.

By providing all of this context, it enables your team to make the best judgment call when they’re at a crossroads.

And you also need to spend time getting in front of the rest of the company and communicating on behalf of your team, sharing what they’re working on, what their successes have been, what their failures have been, what they’re planning to work on, what we’re learning along the way.

You are the voice of your team.

Drive internal and external alignment

And the last major role, drive alignment internally and externally.

Communicate your vision and roadmap to others in the company, so they align with yours.

If they don’t know what your vision is, and what you’re trying to achieve and why, then, why would they be aligned with you?

What would their purpose be?

Build and maintain strategic relationships and partnerships throughout the company.

Those partnerships are really handy when you need commitments from other teams.

Those relationships also help build a tight feedback loop on how the team is doing.

Keep your team aligned on where the business is headed, so their work isn’t wasted.

Staying a couple steps ahead, means your team won’t be left behind.

Be clear on the value provided by work.

It’s easier to get buy-in and commitment when you can speak clearly to the value provided instead of just telling people they have to do it.

This applies to both your team and external teams.

Culture, culture, culture

Next, let’s cover building and fostering team culture.

Culture, culture, culture. You know like the Steve Ballmer, culture, culture, culture. Sorry, I don’t mean to get all Steve Ballmer on you here, but it’s extremely important that you really pay attention and focus towards team culture.

Without a healthy team and company culture, you’re going to struggle.

People will not be happy at work when there is a bad culture at play and you won’t get quality work out of them.

Employees will be disgruntled and most likely leave. Attrition will be real and it will be hard to recover from.

Let’s first talk about trust.

I’ve heard this quote a few times and I love it. “Leaders inspire trust and don’t use control.”

Without trust, eventually, everything breaks down in a bad way.

Control will only get you so far. And most people don’t like being controlled. It’s hard to retain top talent when you’re controlling.

Control also takes a lot of time and energy with diminishing returns.

Usually, the time and energy that you focus on control, you can apply to strengthening trust and get more value in the long run.

Building of trust starts during the interview process. So, there is a baseline of trust on day one of employments. If you don’t have any confidence in their ability and trust that they’ll do what’s right for the company, then why did you hire them?

That trust must continue to grow and strengthen over time. You do that by having their back when things go wrong.

The first time you leave them hanging, and don’t have their back, the trust between the two of you will be destroyed, and it will be extremely hard, if not impossible, to rebuild.

You need to be there for them starting day one. You also need to deliver on your promises to the team. If you can’t deliver on the promises, why should they trust you?

How vulnerability strengthens trust

Vulnerability is also a great way to build trust.

People will trust you more if you could be vulnerable with them. Exposing that part of yourself can be difficult and awkward, but is a great means of building trust.

I’m usually very transparent and open about my failures and weaknesses. I don’t see those as bad things. I see failures as events that I can learn from. I see weaknesses as areas that I can focus and improve on.

Look, we’re continually learning in life. We’ll have successes and failures. The moment someone thinks that they have it all figured out, is the moment they are left behind.

Failures are a key driver of growth

Let’s talk a little bit more about successes and failures.

Again, both provide learnings that can apply to work later on. On our team, we equally celebrate both successes and failures.

That being said, you should not repeat failures because that means you’re not learning or applying those learnings.

So please keep that in mind.

The more open and candid you are about failures and successes, the more others outside of your team can learn from them as well. It’s typically easy to celebrate successes, but let’s not forget about celebrating failures too.

That will help drive culture that takes risks and embraces failures, instead of being risk-averse, trying to hide any failures when they occur and not holding oneself accountable.

Again, these lessons we learn, will help us grow and be better employees.

How feedback creates improvement

You know what else helps us grow?


Let me first start off by saying feedback has…It should be a two-way street. You should be open and ask for feedback just as much, if not more, than you give it.

If you’re not receptive to feedback and act on it, then why would you expect others to be? You must lead by example.

When giving feedback, both positive and constructive, excuse me, put some thought into it before delivering it. You should have some clear examples on why you’re giving this feedback.

There will be times that giving quick feedback in the moment is effective, but that shouldn’t be the norm for constructive feedback.

Feedback should come from a place of caring and for improvements and growth purposes.

As cheesy as it might sound, feedback should be a gift.

You don’t necessarily need to prescribe a fix for constructive feedback. However, you need to make sure it’s clear, what the expected outcome of acting on that feedback looks like. Give them something to work towards.

Then you should continue to follow up on constructive feedback to make sure something is being done about it.

Commend them when you see that they’re acting on feedback.

Positive feedback should be given whenever there is an action deserving a positive feedback, don’t hold back. Reinforce good behaviors.

What is psychological safety?

Psychological safety is another important part of this team culture.

Being vulnerable, celebrating failures, providing actionable feedback, and building strong trust, all lend themselves to psychological safety.

People need to be safe when sharing ideas and new approaches when calling out something they don’t feel is right. Without psychological safety, people are less likely to take risks, and more often than not, the company will not benefit.

Without psychological safety, people are less likely to speak up when they see something is wrong or they feel something is wrong, and it just ends up staying there without ever being addressed.

All these things I mention lead to empowerment. People are at their best when they feel empowered. They’re excited to come to work and make a difference. They come in with creative solutions and deliver amazing work.

Putting these principles into practice

Okay, so now, I’m going to get a little more tactical here and talk about how my team does planning, prioritization, and alignment, how we work with the rest of the company and fit into the overall company-wide process that we need to.

So as a company, we have a quarterly planning that kicks off mid-quarter. Teams start working internally to figure out what they plan to work on during the next quarter and how to prioritize that work.

They start identifying if they need any other teams to support them in that effort. They end up with a plan of what they’re going to do to work, or what they’re going to work on during the next quarter.

I start planning about five weeks into the quarter, trying to get a jump on it. I put together a document with business context to help guide the team on their planning and prioritization. I deliver changes that have occurred within the company over the last quarter, some business impacts that might be coming our way.

So, by having all of this, you know, really more of the what and the why, again, really focusing on the what, the why. That’s what I try and deliver.

The team is free to comment and ask in the document, any questions they have. This really helps to make sure they have a clear idea of the what and the why.

There are three sections I ask them to fill out.

Projects internal to the team, projects we’re asking others to support, and projects that we’re being asked to support.

Oops, sorry.

We then meet as a team to review the what and the why and start prioritizing the projects the team has laid out. Once that is finalized, I have a clear understanding of what the team is looking to take on next quarter, and who we’ll need to support.

I have all the context I need to go out and work throughout the company.

Once my team has identified other teams we will need to support, I go into alignment mode. I start meeting with teams and management to make sure they’re aware ahead of time that we’re going to be asking them to spend some of their time and effort on some tasks. I make sure I’m coming across clearly with the outcomes and the business values of this work.

Clearly expressing value, and getting teams to understand is key, if you want them to invest their time and commit to doing this work, especially if you want them to do it effectively.

Teams will take these asks into consideration as they go into their planning cycle.

Then, a little bit later, there’s another process that kicks off, and it happens about a month prior to the quarter. Where leadership from Product Engineering and Program Management come together to discuss what we’re planning to work on during this upcoming quarter.

It’s a pretty big, large meeting. You know, we’re globally distributed, we have tons of teams, so it’s a lot of folks in a room. It’s quite a bit of content to go through.

Some fun thing that I usually do when we’re going to these meetings is I’ll kick up a thread in Slack to my team and I’m kind of like live-tweeting, but I’m live-slacking. I’m letting them know what some of the teams are working on, what are some things that might come our way, so just trying to constantly have a good flow of that context to them.

So this meeting takes place and it’s also a good venue where we can discuss any cross-functional and cross-organizational work that is queued up for the next quarter.

People are free to jump in with any questions or concerns so that there’s a clear understanding coming out of the meeting.

The next couple of weeks are spent gaining commitments from other teams when their support is needed.

We then meet, as a group, one more time to review any changes that might have occurred since our last meeting.

After this meeting, our quarterly plans are locked in for the next quarter.

Benefits of a Lead Lead culture

Let’s close out. Whoa, kind of went through this quick, all right.

Time for Q and A. Let’s close out by reviewing some of the benefits of a Lead Lead culture.

People doing the work and supporting the work, get to decide when and how it’s done. They’re in the best position to do so, when provided context to help their judgments.

They’re the ones that are gonna have to be running these systems, so why should it be someone else dictating to them how they should be building and deploying these things?

Hiring and retaining talented folks is almost a full-time job in itself when you’re growing rapidly and want to do it right.

This allows a manager to focus on building teams quickly, which is a critical need again if you’re scaling quickly.

Feeling empowered to do things the right way, leads to higher employee engagement and satisfaction. They’re proud of the work they’re doing. They go and they share with people the work they’re doing and the experiences they’re having, which then kind of funnels back into your recruiting pipeline.

So, everyone’s happy.

It leads to career and individual growth.

As you’re fostering a culture of taking chances, and learning from both successes and failures and feeling safe when doing so.

It empowers folks to do what’s right for the business and puts them in a place to be successful. Therefore, this leads to better business results.

Thank you.