First 100 Days as an Engineering Leader

How to Win Your First 100 Days as an Engineering Leader at a New Company (Interview with Steven McCord, Senior Vice President of Technology at WhyHotel)

Jumping on an engineering leadership role at a new company is overwhelming.

Insanely overwhelming!

You want to do your best, learn quickly and make good decisions. You know that the expectations are high.

But even if you try to do your best, you will make mistakes.

So, what are the crucial things you need to pay attention to? What can you learn from other engineering leaders’ mistakes and successes? How can you make this transition as successful as possible?

In this post, you will get answers to these questions.

Our lovely podcast host, Karolina Toth, did an interview with Steven McCord, Senior Vice President of Technology at WhyHotel on episode 12 of the Level-up Engineering podcast.

Steven has made this transition multiple times, and he is openly sharing everything with you so you can avoid the common mistakes and make your first 100 days as a new engineering leader as smooth as possible.

This post covers:

• The challenges of joining a new company as an engineering leader
• Early priorities for engineering leaders
• Focus areas for engineering leaders in a new company
• What would Steven do differently looking back?
• Common mistakes of engineering leaders in a new company
• To-do list for the company to make the transition smooth
• Bonus advice
• About Steven McCord

What do you need to get done as a engineering leader in your first 100 days?

Try not to rush

As a leader, especially if you're an executive, it’s expected to make your mark and to create a plan quickly. In my current organization, it’s fast and furious. I have to make a lot of decisions, and that started the first week I was there. There’s no technology, so they need help defining the vision and the goals, and we need to make choices.

At my previous jobs, there was no rush to make decisions. I don’t like making decisions without understanding the full context, because it could backfire.

Understand the whole context

Tech stack

From a technology point of view, I want to access all the source code. I want to see the documentation to understand the tech stack and the talent building it. I need to see how they write comments and commit code, and I have to see what the architecture is like.

Business

I also look at non-technology aspects, like budget, product features, the product roadmap and current business contracts.

People

To learn about the roster, I like to do one-on-one meetings, including many skip level meetings. I don’t keep doing them with everyone in engineering, but in the first 100 days, you need to get to know the people. It’s a great way to evaluate how talented they are, to understand their motivations and what makes them tick.

Culture

Culture can be a problem in organizations. Once I was brought in to fix the engineering culture of a company. You have to dive deep and find what’s broken. The problem could be the people or the system.

Peers

You also need to figure out what your peer set is like. At the executive level, you need to understand what type of leadership the organization has. It may be a hands-on type of leadership that requires you to dig deep, or it may be hands-off, requiring you to push everything down the ladder. These are different styles, and you need to understand the expectations.

Ideally, you find out all this during the interview process, but you don't always get that luxury.

So, what do I do in the first 100 days of being at an organization? For me, it’s not about perception; it’s about making sure I have an impact and putting together a plan that moves the organization forward.

You need to consider all this when you’re in a new engineering leadership position.

What should an engineering leader to do in the first 100 days when joining a new company?

It depends on the company, but there are two things I tend to do:

Start with the architecture

You have to make sure you figure out your architecture. But you shouldn't rush it. First, you need to understand the business problems.

Wherever I go, I build trust and culture around me. This is interesting in WhyHotel, because it isn't a tech company. Most people here come from real estate and hospitality. It’s a challenge because we’re from different worlds.

I try to breed trust by digging around decisions without tearing people apart. I don’t go and question, “Why did you make this decision?” Instead, I say, “I'm sure there were reasons why we made these decisions. Let's talk about them.”

Prove yourself a team player

You need to prove yourself a team player. I believe as an executive, you have to lead by example. This is how you build the culture.

You have to show them that you're open and transparent about communication. You need to be empathetic and you use your emotional intelligence before you expect it from others. I demonstrate my core values of being accountable and transparent to show my reports the way.

Doing this is very softy-feely. It may sound weird from a technologist, but if you can set this tone and build trust across the organization, a lot of things become easier long-term. If I want to make a big decision, people will say, “I trust Steve; he's honest and works hard.”

Communicate priorities to everyone

Setting priorities is all about leadership communicating to the rest of the company what's important. This is often overlooked. You can’t have everybody interpreting things differently.

At the leadership level, you need to say what’s important, and whatever isn’t on the list is a distraction from them. The main goal that we want to create is uninterrupted focus on people solving problems, especially in technology.

It's an art; it needs immense focus. If people are distracted all the time, being pulled here and there, things don't get delivered. Then you can’t have expectations, and you can’t hold each other accountable.

Align your team and your peers

I have a team of 3 people. I want to set clear expectations on what needs to be delivered, priorities, and expectations. I expect them to make good decisions, and I'm going to hold them accountable to deliver.

If they don't deliver, we should talk about the reasons. Technology is all about delivering value to the customer. If we're not doing that, what the hell are we doing? I set clear expectations about this.

I make sure all the other executives do the same across the company. If the other organizational units don’t do this, it can create churn. It's simple, but it often goes wrong.

However you do it, create focus aligned to your enterprise value.

Bonus advice for the first 100 days of an engineering leader

Build relationships

The one thing we haven’t touched on yet is building relationships. This is what organizations are all about. You work with human resources, sales and marketing. Showing humility in engineering is important; no one should ever be the token engineering asshole.

Showing honest interest in the business or your peers’ discipline is key to this. You should know what their work looks like and how that affects you. The interest needs to be genuine; if you don’t care, don’t fake it.

I'm interested in how different business units run, because you have to put the pieces together. You need to have the product and the engineering strategy coalescing.

Show your worth

Have everyone show the value they add to the organization. This instills confidence throughout the company that you're going to do a great job. The heart and soul of this is to build confidence as quickly as possible about your work.

They're making a bet on you in the hiring process. I fancy myself a good hire, but I've missed too, and you're going to miss 20% of the time at best. So, you have to show them that you're the one to bet on.

It comes down to confidence and trust. If they have confidence in you, everyone will be like, “Steve’s going to crush it. I know him.”

About Steven McCord

I've been in the product technology world for about 20 years. I did R&D early in my career, jumped into product, then back into technology, and led teams of 200 people and teams of 2 people. I've been in the startup world the whole time, focusing on technology and data.

Currently I’m Senior Vice President of Technology at WhyHotel.