No role screams the word "lieutenant" like Chief of Staff -- a position that CEOs (and many other C-level execs) lean on to execute (aka: get it done) and form strategies to help grow the organization. The best Chief of Staffs are both operators and strategists. This Lieutenant Q&A is with one of the best in the business, Michael Arrieta, who is a self proclaimed "Chief of Staff addict". Michael began his career as a sales rep at Cutco when he was 17, became a top lieutenant at DocuSign working with its legendary CEO, Keith Krach, and in March just began his own new venture. In this Q&A he talks about his journey to CEO, saying no, setting expectations, and why not all Chief of Staffs are created equal.

Before we dive into your journey as a lieutenant, tell me about your new company.

Garden City is a purpose-driven, buyout holding company. We buy family-owned service companies in the Southeast from business owners who are retiring or transitioning, help grow them, and hold them forever. Think of it as Berkshire Hathaway meets ServiceMaster.

When we buy these companies, we do three things. First, we instill a servant leader culture where the people who work at these companies can thrive and prosper. We give them a path so they can go from making $15/ hour to one day ideally becoming a general manager or executive. Second, we tech-enable the business. A lot of these family-owned companies have minimal technology deployed. Not because they're not smart or capable, just because it's a different industry, different world, different era. By adding simple tools like DocuSign, SalesLoft, Gusto, or Xero, we can dramatically improve productivity and provide a better customer and employee experience. Finally, we hyper-growth sales. We have a group of 40+ advisors/investors and through their connections we can open almost any door to create new sales opportunities. So, culture, tech, sales.

Let's talk about your personal journey, including your most recent lieutenant roles at DocuSign.

When I was 17 years old in high school, I started selling Cutco knives and eventually became the number one sales rep in Cutco. It not only paid my way through college debt-free, it also got me into my next role. I was a Sales Manager at Wyse, which was acquired by Dell, where I eventually took on my first Chief of Staff role. It was my first time in a role like that and I was young and prideful. I had a lot of ego, and I wanted to be the man. I wanted the glory, to be on the front lines, to be making the decisions. I wanted, I wanted, I wanted… Luckily, the CEO I was working for was gracious enough to coach me through that.

It wasn't until DocuSign that I realized what a true chief of staff was. It's being in service to your principal with anything and everything that helps equip them for success.

When I met Keith Krach he was the CEO of this small eSign company called DocuSign and I was still at Dell. I left the safety of Dell to be mentored by Keith and have a front row seat of building a Silicon Valley startup. I guess I'm a Chief of staff addict. It wasn't until I got to DocuSign and worked with Keith that I realized what a true chief of staff was. It's being in service to your principal with anything and everything that helps equip them for success. The number one currency a CEO has is time. It's the number one thing that neither Keith, nor you, nor I, nor anyone can ever get more of, and I was going to enable Keith to have more time to focus on things that mattered. I was at DocuSign for 6 years, three of those years working for Keith as his Chief of Staff, then moving on to global VP and GM for our enterprise sales group. I did that for almost three years. What are attributes of a great Chief of Staff and what one word would describe the role? Service by far. Being just a servant. When I was with Keith I was his trusted advisor, jack of all trades, his get-it-done guy. Before I started, Keith would take a thousand calls and meetings a day and have a bunch of follow-ups. He had to take notes in every meeting, prepare for every meeting. When I came on, he was able to get away from all of that and just focus on the meetings he had to be in and the decisions he needed to make or facilitate at that specific moment in time. I would say the other biggest word is trust. Without trust, this partnership would have never happened. He trusted that if he was entitling me to take a call or meeting on his behalf, that I would probably make a similar choice to what he would have made. As Chief of Staff, you're a service provider, and a resource to the rest of the company. How would the people you work with describe your leadership style, and is that how you'd describe yourself? I would say the one word is probably efficient. I think the biggest delta of what changed when I joined as Chief of Staff was efficiency. I systemized a lot in the company. Put a lot of processes in place. I project manage the heck out of everything. If we had a meeting with, say, a product manager, Keith would throw out five ideas and the product owner would throw out five ideas. I would capture all those ideas, put them in Asana, assign who was responsible, and track it the whole way through. I think at first people felt like it was too much, but after experiencing it quarter after quarter, they saw it was healthy.

I project manage the heck out of everything.

In terms of how I'd describe myself, I'd say strategic. When I see a problem or an opportunity, it's always multifaceted. I never see anything binary. I'm always trying to figure out how one part fits into the whole, and if it isn't whole, what other parts need to come together to make it whole. Let's talk about stress management. Clearly, the volume that you have to digest, simplify, organize is staggering. Personally, how do you manage that? The first thing is I standardize on saying no. Whenever anybody in the company brought me a new idea, a new market, a new M&A opportunity that they weren't yet ready to bring to Keith, I would just default to no. That weeded out 80% of things. The other 20% were things that people pushed on two or three times. Then I would know there was some substance behind it.

Standardize on saying no...that weeds out 80% of things.

Number two is set realistic expectations, always. Too many people set unrealistic expectations and they just bombard themselves. I would say, "It sounds great, give us a month or two weeks to get back to you." People would ask whether we were really going to get back to them, and I would just explain that we needed the proper time for diligence with other things going on. You've worked with so many great businesses, many very large. Now you're focused on local services businesses. What's your filter: customer, team, or financial-first? It's people-first, all day. If you look at our website it says, "Happy employees equals happy customers equals healthy business." I think that if you focus on the people and you properly set them up to succeed, the financials work out. You have to let them know what is important, which might be profitability, customer churn, upsell, cross-sale, efficiency, and so forth, and then properly equip them and train them. If you give people a place of purpose and belonging, they will want to pursue excellence.

If you give people a place of purpose and belonging, they will want to pursue excellence.

Some 3,000 years ago Aristotle said it well that "people do not relate to directions or orders. They only relate to objectives and motives." It's a noble vision. Once people are bought in, they will go above and beyond for customers, treat them the way they should be treated. Once customers are happy, they don't want to go anywhere else. They're willing to pay more for a service, which obviously impacts the bottom line. I'm such a strong believer in people, I can't even tell you. At DocuSign, we always said words matter. Don't call it a headquarters, call it our Atlanta or San Francisco office. Don't say employees, call them our DocuFamily. Little things like that make a difference. We were hyper-focused on creating a place where people wanted to work at DocuSign, where they could achieve great things. But we also made sure everyone was hyper-obsessed with customer adoption. People were our true North, but we huddled as a team around customer adoption.

I've been in companies in my career that were all financially-driven. Unfortunately, you make the wrong decisions.

If you don't pay people properly, they'll go to competitors. If you're charging customers more for renewals, they won't be satisfied. One of my board members is a founder of the Ritz-Carlton Group, and he wrote a book called Excellence Wins. In it he says "There is no such thing as a business alone. Business only exists for people and among people." You cannot hold a business that does not engage with people. I've been in companies in my career that were all financially driven. Unfortunately, you make the wrong decisions. Let's talk about the future. Imagine you're retired, sitting on the beach somewhere, thinking back on your professional legacy. What do you want that professional legacy to be? I want people to say I created built-to-last companies where people are set up to thrive. I came from a family with three children where my parents never made much more than $50,000 a year. Some of us live in a bubble, but the majority of Americans are in jobs where they do not have opportunities to grow, develop, prosper, and save. I want to create companies where there is a clear promotional path. Where, if you work here, you're being developed and invested in. Where you grow and have an equal level playing field to everybody else. There are amazing companies like that out there, but not all.

I want people to say I created built-to-last companies where people are set up to thrive.

Any tips or recommendations for people looking at a Chief of Staff role? My biggest one is to set expectations up front. Talk about timing, how long you're willing to be in that lieutenant role and what you're looking for out of the role. The biggest rub between CEOs and lieutenants comes from a lack of expectations. Keith and I were very clear about expectations. We had check-ins and total clarity. For example, I knew that Keith and I were at two different stations in life. He had a family with kids. I was married, no kids. When I signed up for the chief of staff role, I was willing to work 80 hours a week and put my life on pause to earn my stripes, knowing that this is a springboard. We talked about it. We made an agreement. If I gave my everything for the next three years, and exceeded expectations, I could write my own path at the company. That's clarity, that's service and that's trust. You also have to know that at the end of the day, you're behind the scenes. Keith told me once, "You have a voice, but you do not have a vote. You have a voice in terms of where the company goes, but the decisions we make are made by me and the executive staff." It hurt at the time, but let me tell you, he was right.

If I gave my everything for the next three years, and exceeded expectations, I could write my own path at the company. That's clarity, that's service and that's trust.

There are some Chief of Staff roles that are highly strategic, and some that are more of a senior executive assistant. I would say a third of them are more administrative, another third are business managers who are operationally oriented, and a third who are an extension of their leader. If that person is on the road, they're stepping into meetings for them, they're taking calls with other CEOs. You have to ask yourself, are you just setting up meetings or are you an extension of the operator? Keith made me get my own EA. That was a big sign what kind of Chief of Staff he wanted me to be. #Growth #Entrepreneurship #Leadership