Why You Need Two Chiefs in the Executive Office

Why You Need Two Chiefs in the Executive Office

Influitive CEO Mark Organ explains how a chief of staff can power up a CEO to superhuman status. Here, he details a roadmap to hiring and training for this critical role.

Influitive CEO Mark Organ was feeling haggard. He’d just raised a seed round for the 12-person marketing technology startup and was rapidly building out his sales department. As the company grew, Organ was becoming increasingly frazzled. He’d forgotten his third meeting in a row and was missing deadlines left and right. His associates told him that he seemed unfocused and wasn’t attending to their needs. They gently suggested he get an assistant. But that didn’t feel right. Organ needed to be several places at once. What he really needed was to be superhuman.

Then it struck him. He’d once seen LinkedIn cofounder Reid Hoffman’s chief of staff Sarah Imbach in action. She’d ran meetings with grace and agility, asking the right questions and ensuring that every attendee had a chance to talk. Organ didn’t just need someone to book his travel. He needed someone like Imbach. Someone who could substitute for him in meetings. Bring him the inside scoop from other departments. Take over projects he was too busy to do. Excited, he began to search for a hire. In the four years since, Organ, who previously founded the IPO’d and Oracle-acquired startup Eloqua and serves on the board of Mobify, has gone on to hire three chiefs of staff (CoS). Alums have transitioned to executive-level roles at the company. Influitive, which now has 125 employees, is thriving — and so is Organ.

The chief of staff role is starting to catch on in the startup world after decades of being common practice in the military, politics and at Fortune 500 companies. Here, Organ breaks down the three types of people you can hire for this role, and how to scope and choose the best person for this critical job. He lays out pitfalls to avoid in the process and gives a step-by-step approach on how to most effectively manage your chief of staff. Organ also spells out when you need a CoS (and when you don’t need one), and explains how to help transition them when their tour of duty is over. Let’s get started.

Scoping the Job

Let’s kick off with the basics: what’s a chief of staff, exactly? It sounds like an elusive title, and that’s because, well, it kind of is — there’s a lot of variability in the type of person you can hire for the role and what that person will do. “The chief of staff role is an intensely personal one. This is a position scoped for the CEO, and it has elements of both an executive assistant and a COO. Like an EA, a chief of staff works only for the CEO and doesn’t have direct reports, except maybe an intern or executive assistant. Like a COO, a CoS works on strategic and critical items, working with employees as well as customers and board members. To be very clear: while the CoS makes many important decisions and has strong leadership skills, this is a service role. The job is to make me a superhero. That means I’m front and center,” Organ says. “I can make better and faster decisions thanks to their work. I’ve got a lot more of the insight I need. I’ve got a greater ability to drive high performance by developing deeper relationships with my team. I’m better able to hold people accountable to their commitments. I’ve got this person whispering in my ear every day, telling me what to focus on and giving me key insights. They help lead the company from the shadows.”

While it can and will vary, here are a few high-level responsibilities your CoS will have:

  • Ensure the CEO is working on the most important items for the company.
  • Help complete priority items for the CEO to an appropriate level of quality.
  • Keep the CEO accountable for commitments, while helping keep reports accountable for results.
  • Keep the CEO accessible and open to new ideas and proposals.

Unique to this particular hire is its rotational status. A typical tour of duty for a chief of staff is 18 months at Influitive. After that, they can transition to another role within a company, often in a position of leadership. One former Influitive CoS is now the company’s director of market expansion, while another alum became the VP of Europe after serving as VP of talent.

Your chief of staff’s background can span a range of experience and seniority levels, so know the different packages this role can come in. Organ gives these three points on the spectrum of hires you can make:

  • A manager-level hire. This person would be responsible for typical administrative tasks like calendar management and booking travel, but he would also make important judgment calls on how the CEO should best spend her time and what meetings would be most valuable for her to attend.
  • A mid-career, director-level hire. This person may have 6-12 years of experience. He would be in charge of tasks like running town halls, preparing speeches and prepping the CEO for leadership meetings. He’s unlikely to take on any strategic responsibilities, however.
  • An experienced VP-level executive. This person is already an experienced executive who’s looking to become a CEO one day. She may meet with department heads to talk through goals and targets, and work on developing tactics for various parts of the business.

Here are broader responsibilities carried by a stellar chief of staff:

Ensure the CEO is prioritizing the right things. “They do that by understanding what’s really going on in the business, internally and externally. I’m more of an externally-oriented CEO — I like closing deals, interfacing with customers and hosting events. So my chiefs of staff spend more time understanding the internal dynamics and where I need to focus my attention, though they’ve also done customer tours and reviews of our satellite offices when I’ve needed to spend more time at headquarters,” Organ says. “They’ve played a critical role in internal matters. Earlier on, we had a management team that wasn’t gelling very well. My CoS at the time, David Axler, did a phenomenal job of helping me build a cohesive senior leadership team. He initiated daily lunches and coffees with every employee in the company to gain insights on how the team was performing. He organized team-building offsites where the senior leadership team was coached on how to be more open, vulnerable and direct with each other. Then he followed through to see that the changes that were initiated were sticking. The impact of gelling a new senior team like this is impossible to overstate, and I couldn’t have done it on my own.”

Level up the executive team. “A great CoS enhances and raises the game for the entire leadership of the company. They do that by providing effective feedback on ideas and proposals from team members. Sometimes they push back when the analysis has not been well thought through. In those cases, they pitch in and help make them better. They also let me know when someone is doing an exceptional job so that I can praise them specifically and effectively,” Organ says. “You need someone who can help you tune in internally. You need someone to be your eyes, ears, hands and feet in terms of developing and hiring the right people. I needed a person to identify rock stars to invest in and uncover mis-hires earlier to get them off the bus faster. A good CoS is constantly monitoring the health of the organization and making specific recommendations on how to improve it.”

Amplify and improve the CEO’s communication. “A CEO spends most of the day communicating, so effective communication is a big part of the job. Presentations need to be comprehensive and crisp, particularly for important communications to boards, town hall meetings, critical customers and analysts. A little effort can improve the effectiveness a lot. I look for storytellers when I hire chiefs of staff,” Organ says. “I recently had a board call, and usually I prepare a small deck that I send to my board members. But this time I had my current chief of staff Bronwyn Smith do it. I expected to have to spend two hours editing her work. Turns out I had to do exactly zero work on this deck. It was unbelievable. She said everything that I would have said — and that she had heard during our time working together. Her analysis was spot on, and it saved me an immense amount of time and trouble, equipping me to effectively communicate at an important meeting.”

Act as a stunt double. “A chief of staff creates accessibility and availability in a CEO’s schedule. He must be an effective substitute for when the CEO is needed — whether that’s at key internal meetings or client onsites. Train them to think the way you would think by sharing the logic behind your decision-making. Seat them in your office and muse out loud. They should know at all times what’s important to you,” Organ says. “As the chief of staff gets more comfortable in this role, you’ll start to see that they start to shine at this. People will start requesting them to facilitate meetings, or sit in on important customer calls. I’ve seen this happen with all three of my chiefs of staff, and it’s not only a great feeling to see them grow, but it’s also a huge relief to know that the company is in good hands when my back is turned.”

Do whatever needs to be done. “It really takes a can-do, will-do attitude to do this job. Some people can’t handle that. It’s not all glitz and glamour. While I would never have a chief of staff do a job that I haven’t done myself, the tasks you assign them can range from high level to basic,” Organ says. “One memorable example is when I decided it would be a great idea to shoot plush unicorns out of an air cannon for a talk at a startup festival. David rented the cannon, bought the stuffed animals and got them shipped to Montreal. It was a big hit, but someone had to handle the nitty gritty of coordinating the stunt. That person was my chief of staff.

Mark Organ shooting plush unicorns out of a cannon at a startup festival.
As CEO, I’m the one on stage. I’m doing the tap dancing. If my chief of staff is doing her job, I get an encore.

When You Need a Chief of Staff

It can be hard to know whether you need this particular role. It’s possible you only need an executive assistant, or you may need a different executive-level hire entirely.

According to Organ, here are some signs you need a chief of staff:

  • Your team is getting bigger and harder to manage.
  • You’re growing after raising a seed or Series A.
  • You’re wishing you could multiply yourself and be everywhere at once.
  • You’re harried and burnt out because too much is on your plate.
  • Your employees are pressing you for decisions or deliverables that you aren’t hitting.
  • You want to be more effective but aren’t ready for a COO or second-in-command.

Here are some signs that you don’t need a chief of staff:

  • You’re very price-sensitive — this hire could cost $75,000-$200,000+.
  • You’re pre-product-market fit.
  • You’re not ready to scale your company.
  • Your executive team configuration doesn’t allow for an effective chief of staff — for example, strong personalities that might prevent a CoS from getting her job done.

Ultimately, though, it’s a judgment call. “This is a high-risk, high-reward hire. Most likely you’ll know when you need a chief of staff. You’ll feel that void where you wish you had someone helping with certain aspects of your job. Don’t confuse that need for a different executive hire,” Organ says. “I’ve seen startups hire COOs when really they needed a CoS to augment the CEO’s capabilities. In a small company, senior leadership team members join because of the CEO and want to report to the CEO, not a COO or second-in-command. Use these guidelines to carefully determine what role is most needed on your team. The more thought you put into it, the higher your chances of making the correct call.”

Scoping Out the Role

If you’ve chosen to bring on a chief of staff, then it’s time to kick off your hiring process. Begin by determining where you need a chief of staff to be especially strong. Perhaps they have strengths that are your weaknesses, or they’re particularly talented in an area that’s currently important at your company. “You’ve got to analyze. What are the key things? Do I need strong communication? I might need someone who’s talented in that area, like Reid Hoffman’s former CoS Ben Casnocha, who’s now a renowned author and speaker. Do I need somebody who can run a department? Do I need somebody who’s really strong in organizational behavior and gelling the team, an executive coach type?” Organ says. “When I was hiring my second chief of staff, I realized I needed someone with really high EQ, who could help my leaders gel better. We had new hires who weren’t completely aligned, and disagreement was frequently bubbling to the surface. So I hired David. He’d done organizational design and managerial effectiveness in his previous work. He’d once handled a project co-led by a European company and a American company. The operating model was completely ineffective, and both sides essentially hated each other so much they couldn’t be in the same room. Within three months he had everyone committed, smiling, working well together and back on track to the critical path. I heard that and said, ‘That’s my guy.’”

Organ has a few tips to kickstarting your search. First, ask yourself these questions:

  • What’s the vision for myself as a CEO? Where do I want to go?
  • What do I most need help with?
  • What don’t I want to do that I’d like to delegate?
  • Am I prepared to give someone access to every corner of my professional and personal life?

Once you’ve scoped out what you really need and want in this role, put the word out for candidates. Market the job as a fantastic way to gain hands-on management experience. “Our belief is that this is a strict 18-month tour of duty. Usually by that time they’re such effective leaders that it’s useful to the company to have them run something else while recruiting a new chief of staff,” Organ says. “Being a chief of staff is a way to accelerate your career growth. If you leave the company, the world is your oyster — you can become a founder, CEO, COO or a VP. It’s very versatile training.”

At the beginning, Organ likes to do an initial interview screen. In the past, he’s also hired a consultant to screen candidates. Because he’s looking for someone who’s decisive and can motivate people, he designs the interview around that characteristic. Here are some questions Organ likes to ask at the start:

  • What’s the most difficult decision you made over the last year? How did you make it?
  • What’s the worst decision you’ve made in the last year? How did you recover?
  • Tell me about how you’ve been able to motivate somebody who wasn’t particularly motivated. How do you make that work?
  • How do you know that a project is well thought-out? What kinds of questions do you ask?
  • If you have a proposal that’s missing some key elements, how do you deal with that? When do you dive in and help a person produce better work? When do you push it back and say, “You really haven’t thought this through — come back when you’ve thought through this some more”?

Dig for answers, but don’t put too much stock in an interview. Your next step is to assign them a project. “It’s very effective. Simulate the job, and have them do it. That’s particularly important in the chief of staff role. For my first CoS hire, we designed an assignment: put together an event for determining Influitive’s product direction. The winning candidate, Fraser Stark, worked with one of our managers to put together this event. After that, we knew he was great. He pushed back on the right things. He asked all the right questions. People on my team who worked with him said, ‘This felt really natural. We produced a much better product with him,’” Organ says.

“A project is a better way to evaluate somebody than asking a bunch of canned questions. One of my other candidates that I thought quite highly of didn’t really enjoy the assignment. He’d been a CoS in politics, and thought it would be really fun to go to a startup,” says Organ. “We quite liked him, but he came out of the assignment and said, ‘This is way too ambiguous. I didn’t really enjoy this.’ I said, ‘You’re not a good fit for the job then, because we do this all day long. We deal with an incredible amount of ambiguity, and we’re looking to you to create order out of that chaos.’ The assignment helped us suss that out.”

Managing Your CoS

Once you’ve made your hire, it’s time to manage training and build your day-to-day rapport. The relationship between the two of you is crucial, so make it as close as possible. “I interact intensely with my CoS. First, they sit in the same office with me, listening to my musings about our challenges. They listen in on my phone calls and attend my one-on-one meetings unless specifically dismissed by the person I am meeting with, which doesn’t happen often. They can also read my emails,” Organ says. “We probably Slack 10 to 25 times per day. I don’t hold back and I tell them everything. They have to know me and how I think. The goal is for the CoS to be able to predict how I would make decisions.

Organ provides the following tenets to create the best relationship and workflow possible between your chief of staff and you:

Write a roadmap for your 18 months. “In the first six months, it’s a good idea to limit ‘stunt double’ work, where they’re basically subbing for you in meetings. It takes time for the CoS to develop the knowledge and credibility to be effective in both internally and externally representing the CEO. If you throw them in the deep end too early, they may not have the consensus needed to lead,” Organ says. “Months 6-12 you should be in high gear. At this point they’ll have built the relationships they need with other executives, and have enough experience to be flying more solo. Then, after 12-15 months on the job, it’s time to think about the next tour once the 18-month term is over. Start talking about what they want next. Once you know that, make sure they’re developing skills relevant to their next job in their final months. Finally, task them with finding their replacement around the 14-month mark.”

Organ's suggested timeline for how to manage your chief of staff.

Structure your time intentionally. “Every Monday morning, my chief of staff and I have a half-hour meeting to go through the week together. We decide which meetings we will attend together or alone, when it makes sense to travel, who we need to spend time with and the goals for these meetings. In general, if it’s an external meeting where there’s a prior relationship, I need to attend the meeting personally,” Organ says. “We also go through the various projects we are working on, get sideways projects on track and figure out what we can delegate. We discuss performance of team members — who should have direct recognition and who is unhappy. All of this creates smoother sailing for you and for your company.”

Present the chief of staff role in a way that sets them up for success. “People generally won’t be offended when you hand them off to a high-caliber chief of staff. Sometimes it’s even preferred! There tends to be better follow-up than when an absent-minded CEO is taking the meeting,” Organ says. “It’s all in how you present it. The language that we use is that the CoS’ job is to prioritize the effort of the CEO. Let everyone know that this person is the one who has your ear, controls your schedule and prioritizes your work. The better you communicate that, the more people will warm up to the idea.”

Your chief of staff is your ambassador. He’s your stunt double. He’s the next best thing to you.

Open up so your CoS can best assist you. “You have to trust this person completely, so hire someone you feel completely safe with. You have to have to be secure and confident in yourself. Then be super open and vulnerable. You must want to see your chief of staff succeed. Tell them what’s on your mind. I spend a lot of time with them. Sometimes we just talk about random stuff, other times it’s more focused,” Organ says. “I’ve logged at least three hours talking to Bronwyn over the last month about all the different board members. What are their issues? What are their fears about me? She knows my deepest fears about my board members. She knows what I’m excited about. She knows everybody’s personality. That’s because I talk to her constantly. She’s a key confidante. If you want your chief of staff to succeed, don’t hold anything back.

Don’t be threatened by their success. “Bronwyn has blown through all of my ridiculously high expectations. She’s been with me four months but is performing as if she’s been here a year. If you’re an insecure CEO, and unsure about your place in the world, having a powerful, effective chief of staff might actually make you nervous. You’d be like, ‘Man, she wants my job,’” Organ says. “If you find yourself in this scenario, check yourself before you wreck yourself. My job is to surround myself with the best possible people. I’m not threatened at all by Bronwyn being able to produce a deck for my board of directors. Those are my bosses, and she produced a better deck than what I’d ever do alone. Instead of frantically making a board deck for the last two days, I’ve been with people. I’ve been walking the floor. I’ve had a couple extra calls with customers that I would not have had, because you know what? She produced something that normally only I could do.”

Listen to your instincts. “I still am what I am. Every now and again I’ll still tell Bronwyn, ‘With all due respect, I know you want me to do X. I don’t feel like doing X. I’m going to go visit some customers. Bye.’ I do have good instincts, and I respect them. That’s an important thing that a CEO learns — when to listen to that inner voice,” Organ says. “At the same time, your chief of staff will have a powerful voice, too. And that’s to your benefit. It’s fine to disagree at points, but for the most part, your CoS and you should be a well-oiled machine. Bronwyn and I are practically a two-headed monster. I trust and listen to her input, but there are times you have to make a call that goes against their assessment, and that’s okay.”

A stunt double is still not the real thing. Sometimes people just need you — really you — in the flesh. “I got some sharp feedback the other day. A colleague said, ‘Mark, Bronwyn is not a replacement for you. She does a great job, and we like her, but sometimes we need you — actually you. I took that to heart and now I’ve set up weekly lunches with different departments. Bronwyn actually helped me come up with that idea,” Organ says. “I always felt that having a chief of staff made me way more accessible. There’s some truth to it, but what we’re learning more how to answer is: when do people need me in the flesh, and when should Bronwyn take it? It takes a lot of trial and error, but it’s important to nail.”

Influitive's current and former chiefs of staff with CEO Mark Organ. From left to right: David Axler, Mark Organ, Fraser Stark and Bronwyn Smith.

Transitioning Your CoS

Finally, at the end of 18 months, it’s time to start transitioning your chief of staff. “While it may be hard to let go of someone who’s been so critical to your success, it’s for the best. At this point they’ll be antsy. It starts to get confusing after awhile. For Fraser, he often facilitated meetings, and people became unsure of his role. Is he my representative, my proxy or is he Fraser? After a while, Fraser didn’t even know who he was,” Organ says. “About 12-15 months in, your chief of staff will likely have an identity crisis. If they don’t, you probably don’t have somebody who’s going to be a future leader in your company. They’ll be gaining more confidence in themselves. In this case, others were gaining confidence in Fraser. People were asking him for advice, not because he was a sort of psuedo-me, but because he’s brilliant in his own right.”

While there’s no formal roadmap for the transition, Organ’s chiefs of staff have gone into executive positions. “Usually at the 15-month mark, I start taking my chief of staff to dinner. Over the course of three or so dinners we’ll talk about their interests and what they hope to become. Fraser was interested in talent, so we made sure he was picking up skills in that area. The same went for David and general management responsibilities,” Organ says. “The best chiefs of staffs do the job because they’re attracted to the rapid career development that’s possible. It is the fastest opportunity to grow because they learn from the CEO’s vantage point — even senior VPs don’t get to see that. Chiefs of staff are massively overrepresented in the top echelons of the Fortune 500, the military and politics. The same will happen for startups: people who have done the chief of staff tour of duty will disproportionately become the most successful founders and CEOs.

After 18 months of being your stage manager, it’s time to let your chief of staff lead. It’s her turn to take the stage.

Be Chief of Your World

A chief of staff takes control of a CEO’s schedule and priorities. She’ll whisper hard-won insights and instruction into your ear and work to help you lead the company from the shadows. Start to look for a CoS after your seed or Series A. Determine where your needs land on the spectrum between an advanced EA and a VP. Hire the right person by giving them a real assignment, but first define a vision for yourself as a CEO — and suss out what strengths your company needs most at this time. Build the closest relationship possible with your CoS by opening up everything from your email to your deepest fears. A good chief of staff will be a trusted confidante and advisor, but always listen to your own intuition. Let them wrap up their tour of duty by finding their replacement. Transition them to a great role in your company that aligns with your needs and their desires, and then get ready for your next CoS hire.

“My level of focus has completely shifted in the past four years. Before I had a chief of staff, I’d float, saying, ‘I feel like talking to some customers,’ or ‘I wonder what’s going on in product? I’m just going to go mosey over there and see what’s going on.’ Now, there’s much more purpose and intent. I’ve got somebody who really knows what’s going on, who tells me ‘This is what you should be doing right now,’” Organ says. “It’s brought me a firm feeling of calmness and security. I’m giving better service to my customers and my employees. It’s my job to provide a great experience for others, and now I know I’m doing that. That was always my intention as a leader, but not always the reality as a human steering a fast-evolving company. My catalysts have been my chiefs of staff.”

Photography courtesy of Influitive.