Few transitions are as difficult as transitioning from being a manager to a leader. Manager to leader - what’s the difference? There are overlooked prerequisites that make these moves hard and often result in missed expectations. According to Gartner, 49% of people promoted within companies underperform up to 18 months after promotion.
Becoming a leader requires a change in mindset, capabilities, relationships, and focus.
I share 5 principles to accelerate your next level of growth on your journey to becoming an exceptional leader. You’ll get smarter faster, be more effective, and succeed for yourself and your organization.
The expectations of you as a leader differ from those of a manager. Managers are expected to be tactical and action-oriented. Leaders are expected to be strategic, visionary, influential.
Early in my career, I got a coveted promotion in consulting: engagement manager. One of my first assignments was to lead a team to craft the strategy for a multi-billion dollar merger.
I no longer simply executed the strategy - I set it. I was also responsible for managing client relationships, mobilizing and motivating my team, creating an environment for high performance execution, and managing upwards to senior leaders.
I learned quickly that the capabilities that got me to my role were no longer sufficient.
Focus less on how to solve a problem. Focus more on defining and deciding which problems should be solved.
In the first two weeks of the project everything seemed to go awry. Client leadership were misaligned, bankers wanted to push up timelines, deal assumptions and deliverables were constantly changing. The scope, scale, magnitude of complexity, and responsibility felt overwhelming.
I needed some serious coaching. I called the Partner in charge of the project.
Me: “I’m managing the situation and stakeholders as best as I can. I’m quarterbacking, but the plays aren’t landing. Things are going south.”
Partner: “sometimes you need to be the quarterback. Other times you need to be head coach or general manager. Watch from the sidelines, observe the people and situation, and re-strategize the play”.
Anyone close to me will tell you that sports, especially American football is not my strong suit. But the analogy made sense. I was experiencing a new dimension of growth, one that felt familiar, yet distinctly different.
I needed to shift from running plays to recognizing when to shift roles and influencing the game strategy and dynamics.
As a manager, your focus is on designing process and tactical execution. As a leader, your focus is on aligning people, driving clarity, and influencing outcomes.
This requires you to think fluidly - zooming in and out of details, inferring patterns from various data points, and generating conclusions that lead to decisions. It also requires you to have the confidence to “call timeout”, regroup the right set of thinkers and players that can help you draw up new plays.
An HBR Study found that 70% of employees are most engaged when senior leadership continuously communicates strategy.
Pro tip: You don’t need to know all the details; but you do need to know how to ask questions that lead to meaningful insights. This will help you define the people who can give you the right insights on work that should be done to deliver exceptional results.
Leadership is a team sport. While there are many books on leadership (Developing The Leader Within You 2.0, Good to Great) there’s no playbook for every scenario you’ll encounter. You’ll need a set of people you can trust and with whom you can bounce ideas.
Why should you have more than one person to reach out to? I believe in having a set of thinking partners.
You’ll encounter scenarios that will require you to have different leadership modes and outcomes. In one day expect to make swift decisions, learn a new domain, deliver tough news, or be an inspiring speaker. Each of these require different capabilities.
In my situation, I looked to the project Partner for coaching on overall leadership acumen. I also tapped subject matter experts in my client’s industry to sharpen my technical acumen and understand success factors for similar transactions.
Having a set of trusted mentors that you can reach out to and help you get smarter faster is mission critical.
One of the most distinctive shifts from managing work products to leading an organization is making decisions that are good for the business as a whole.
Your performance is tied to the performance of the entire enterprise. This means you’re dependent on lots of teams and people to make you successful.
You’ll have a deeper sense of how you might partner for better shared outcomes. You’ll also learn to speak and understand the language of other functions. This is important as you’ll be in a better position to make trade-offs and explain the rationale for decisions.
In my scenario, I set a learning plan to broaden my perspectives. As I expanded my mentor circle, I asked for additional names of people with whom I should connect to learn more deeply about a topic.
Here’s my tactical plan that I recommend you leverage:
Pro tip: tap people outside your firm who have a similar role. This helps with alternate views to compare and contrast approaches.
“Time is the scarcest resource and unless it is managed nothing else can be managed.” Peter Drucker
How you allocate your time and your presence is crucial for your effectiveness and for the success of the organization you lead. Where you spend your time is also a reflection of how you lead and what matters most to you -- which trickles down to the organization.
The key to spending time on what matters most is to make room for those things.
Critical question: how do you spend your time now?
In my example, I took an inventory of meetings I attended, activities I spent time on, and compared these to achievement points. I found that I needed to reallocate my time to more value added areas that enabled important priorities: reset strategy, align stakeholders, re-direct my team. (see principles 2, 3).
Read: How CEOs Manage Time
The transition from manager to leader is an exciting journey. It’s also hard work. Don’t make the mistake of thinking you simply took on a similar job with larger scale and scope. You took on an entirely new responsibility with a new set of performance measures and expectations. Be proactive about attaining the next set of tools for your success toolkit.
Before joining, I tried to read what I could about Chiefs of Staff at tech companies. Ultimately, I had no playbook and was nervous/hopeful that I would do a good job. I had to take it a day at a time, and just figure it out along the way.
Though I know the experience will be different for everyone, here’s my contribution for anyone interested in what a CoS does at a seed/Series A startup, and how my role evolved over time.
I recently read that anxiety is responsible for driving us forward to succeed. During my first month at Dover I was driving a little too fast. I grasped for things to do, feeling I had a lot I needed to prove, but soon realized there was a better way for me to approach things.
I pulled the car to the side of the road and gave myself permission to lean back. I strived to listen more than I talked, and think more than I acted, telling myself to be patient, slow down, and observe.
When I joined, our CEO (Max)’s calendar was full of sales calls and first phone screens with Dover candidates. There were also random clerical things that needed to be dealt with (cancelling bills, dealing with movers to close our SF office, scheduling meetings, etc.) Dover had also not done any marketing.
My first order of business was to shift these things onto my plate. To build trust and to free time for others, I took on the administrative work alongside some of the more exciting areas like marketing that had a lot of greenfield.
At the end of my first month, I did the marketing launch for a free tool which was a nice first win. This launch outperformed some previous ones we had done and resulted in our highest traffic website day up to that point.
I closed my first sale on September 13th. By this time, my calendar had become a back-to-back block of 30 minute calls all day — split between new sales conversations and candidate screens. Max’s calendar was clearing up.
Repetition is the mother of learning. I spent all day pitching Dover to both customers and candidates, answering questions and handling objections. So I had started to build enough context to contribute to strategic conversations. My goals evolved: I had abstracted tasks away from Max, but now I wanted to be equally as effective as him.
By the end of month 2, candidates I had first rounds with were progressing into late stages, and I had the opportunity to be part of their onsites and final evaluations. In preparation for their joining, I started to build out our employee handbook.
Around the 3/4 month mark is where I started to see the magic of the CoS role. Our financial analyst, Frank joined in late October and took over contracts and other tasks related to sales Ops. Something that I had been a stop-gap for was now successfully handed off! That was cool.
Around the same time, Dover was experimenting with an “interviews product”: we had hired four people part-time to conduct first round candidate screens on behalf of our customers. Since we use our own product, I was able to start handing off internal first round phone screens to our Interviewers after conducting more than 100 calls myself! Again: where I was once focused on executing, I shifted to training others, and was free to think strategically about how to improve the process or product I’d just handed off.
Also in October, I launched another free marketing product with similar success to the previous one. We had another peak day for site traffic. In the time I had left, I wrote blog posts and got at some low hanging fruit to make our website, JDs, and employer brand stronger.
With my first 90 days down, I wanted to check in with myself. How had I done, and where was I going? This is when I decided to reach out to other Chiefs of Staff and interview them for an article. These conversations helped me define how I could be better, and what I should be striving for.
Ringing in the new year, I felt I had earned trust and started to experience flow. If my goal in previous months was to absorb our CEOs tasks, and then to be equally effective, I now felt like I was adding my own signature to things. I started to establish my own playbooks and felt the imposter syndrome fade.
Sales and Management were my two biggest responsibilities at this point. My AE workload had gone from taking up 30% of my time to 70% as inbound customers continued to pound the door. The team of 4 interviewers we had experimentally hired were working out great and customers saw value in the new product offering. So we quickly hired more people — and the growing team needed a manager. I focused my remaining time on being a stand-in for this.
At this time, People Ops was suddenly becoming more necessary. This included things like facilitating team events and bonding opportunities, orchestrating the onboarding of new team members, and later reviewing and improving those processes through feedback. I responded to thoughts and ideas as they came up.
In January, Max put a daily 1:1 on my calendar. Our working relationship got better as I got more insight into what he was doing, what I should be doing, and what was coming up. Being a remote CoS can feel wobbly — you wonder whether you’re working with complete information — so at this point, the extra time was helpful.
By February, I’d already seen my role and responsibilities evolve several times, and I could see another big change on the horizon with the possible addition of several new employees. Wanting to take stock of things, I did a sort of “audit” on my role, reviewing all I had accomplished in my core areas (Sales, Marketing, Hiring). I learned a lot about the impact of my work that had previously gone over my head.
Other Chiefs of Staff called out to me in our interviews “if you’re doing the role well, no one will know.” Chiefs of Staff therefore need to be proactive about making sure the right people know what they’re doing. So in March, I had a conversation with Max to share what I’d learned.
By April, Dover was 23 FTEs (triple since I had joined), and by May, it was time to establish our company values. I worked with our CTO to create a process for uncovering and solidifying them, then lead the workshops with our broader team. We were starting to feel like a ‘big’ company!
The contract interviewers team was growing, too. We were 12 people and counting by this point, so I appointed three Team Leads to assist with some of the ‘people’ aspects, and focused on being a liaison between the interviewers feedback and the product team building workflows for them.
In the spring, Dover supported me in going through the Coho Chief of Staff Fellowship and I was able to represent Dover at the YC GTM Expo. By this time, daily syncs with Max were no longer necessary, so we paired down to meeting once a week.
In June, we hired our first growth lead, Harry, to take over Sales. Our second growth lead, Bryant, came shortly after. This was a big deal as it meant I’d be stepping back from the day to day work of the department I’d been most focused on.
I had done short, simple trainings with other new employees as I handed off small things here and there. But this would be different. I worked closely with Harry, investing myself in ensuring he was set up for success, being an ongoing thought partner. By the time Bryant joined, Harry and I were able to share some of the onboarding responsibilities. With new sales officially off my calendar — I turned myself toward Account Management and Strategy.
In July, Mario joined as our first operations manager. Our contract interviewer team had grown to 22, and where I was previously a make-shift stop gap for managing them, Mario would be a dedicated leader for that team.
The majority of my time early Summer was spent on onboardings for Mario, Harry and Bryant. I saw my role start to transform again as in my free time, I was able to jump into what I call “strategic projects” — the random one-off side projects that are high potential for Dover and need to be proven out. I saw myself becoming the end of escalation paths, and striving to be a true stand in for our CEO on various issues/a final decider.
Over the summer, we opened an office in New York City, and announced the close of our 20M Series A.
This month marks one year at Dover, and I am very happy with how things turned out. My goal coming in was to observe and understand how a company scales from point A to point B, and to be a core part of that growth with the ability to point to things and say “I did that!”
I’m excited to see where we go from here and see what else I am able to accomplish in this role.
I mentioned early on that I did not have a playbook for being a CoS at a seed stage co. So here are a few of the things I did that I think made the difference for me.
This is especially so because I graduated in computer science from UC Berkeley, but joined a news-and-media company instead of a tech one. Naturally, then, such questions arise. I’ll try to answer them here, though, at a 30,000 feet level. As Chief of Staff to Vice Chairman at one of India’s premier media conglomerates, I’m fortunate to contribute to high-impact projects, lead some strategic initiatives, and in essence, help my mentor scale up.
But even as I answer these questions, a part of me feels they are flawed; they assume that the CoS has quantifiable, measurable KPIs, like an engineering manager. A CoS does not. Rather, a CoS's KPIs are meant to be qualitative and are often immeasurable, as they vary from industry, company, context. A CoS's KPIs may not be strictly valued but they are valuable, or else the role wouldn't exist in the first place. Tanya Reilly put it best when she called this phenomenon glue work: “the less glamorous – and often less-promotable – work that needs to happen to make a team successful.”
So, the problem at hand is subtle: The CoS is supposed to make everything work. If it all works, great, and you move on to the next project; if it doesn’t, it’s your fault, at least at some level. Not that you’ll be directly held responsible for it, but you’ll feel that some glue work could have helped the project succeed. Now, this is an interesting dynamic. A CoS is like the orchestra conductor who brings out the best in each musician; when the orchestra succeeds, musicians succeed, but when it doesn’t, the conductor fails. Through the prism of this intriguing dynamic, we will explore the CoS’s role + KPIs, and answer these two common questions: What do you do as CoS + What are your KPIs.
A CoS is a senior advisor who coordinates among stakeholders, helps oversee high-impact + critical projects, and serves as a liaison between the company's senior management and other executives, all the while ensuring that the company's goals are met. In short, the CoS is responsible for work above and below the 'call of duty'. In such a case, glue work matters much more than non-glue, quantifiable work. Here, sales targets fade when compared to resolving a high-impact regulatory challenge, or negotiating agreements, or divesting assets.
As CoS, you need to think about how to align the organization's KPIs with its overall goals, and how to ensure that progress is made toward achieving those goals.
The CoS's KPIs, then, naturally become qualitative, and for lack of a more accurate description, "fluff". Yet, this 'fluff' has immense depth beneath it, once you understand the context in which a CoS operates, and the high-leverage that the CoS's work has. For instance, communicating well across different teams and aligning them to work together on a complex problem ends up as a more non-trivial problem than, say, meeting X thousand dollars in sales targets for Q1. The former sounds lackluster; the latter fancy, but in terms of impact, the two differ. Now, of course, this is not to say that one piece of work is definitively more impactful than the other... In another context, the CoS’s role would be less valuable than the salesperson’s role. So, context matters. This example is to demonstrate that quantitative and qualitative KPIs have different degrees of impact, and that one is not necessarily superior than the other. It all depends on context. Now, as a corollary, let’s understand the KPIs of a CoS.
Another example of a CoS's nontrivial KPIs is establishing priorities. At senior levels, when you are constantly context-switching and dealing with a flurry of dynamically-evolving situations, you need to be able to prioritize. A CoS helps senior management do just that. In fact, here's a hypothesis: The CoS enters with no KPIs as such, but over time, builds his/her own KPIs whilst also creating the same for others.
At senior levels, when you are constantly context-switching and dealing with a flurry of dynamically-evolving situations, you need to be able to prioritize. A CoS helps senior management do just that.
In that sense, a CoS gets to deal with ambiguity, manage esoteric knowledge, handle subtle situations, and crystallize the abstractness into concrete next-steps. For instance, how you translate the problem of "employee motivation in a company in flux" to meaningful next-steps like "compensation rewards, post-flux bonus, retention schemes, elevated titles, and ESOP proposals" is an important element of the CoS's skill-set.
I would go a step further to say that as you proceed in role seniority, you need to deal with more qualitative KPIs than quantitative ones. For working on the right thing becomes more important than working hard but on the wrong thing.
The CoS translates strategy into principles into tactics into actions, spanning the wide expanse of turning chaos into order, ambiguity into specificity.
In essence, the role of a Chief of Staff is to provide support to senior leadership, co-lead special projects and initiatives, build relationships with key stakeholders, provide insights, facilitate communication, and monitor risk. Above all, the role of a CoS is to identify what matters, because helping the key executive work on the right problem is more important than making them work on the wrong problem. The CoS’s role contains both qualitative and quantitative measures, all of which together help the organization move in the right direction.
As CoS, I’ve been fortunate to be exposed to a variety of business problems in complex and challenging environments. Of all things to remember for being an effective CoS, though, perhaps the most useful one I’ve learned is how to deal with ambiguity. When problems are loosely defined, end-goals are amorphous, and their impact immeasurable, how you operate will reflect your future success. Understanding that the CoS’s KPIs are, by definition, unique, will help you be at ease and effective in your dynamically-evolving role.
In 2013, following a few years of bouncing around, he found the path of entrepreneurship - opening his own design consulting business. Over the next few years, John would learn how to run and grow a company by the art of action - quickly learning how to put one fire out after another. This accumulation of knowledge allowed him to create his second business - a news media company that covered the tech, innovation, and entrepreneurship community titled StartNow Pittsburgh. While running both simultaneously, his continued efforts sparked a deep passion for building businesses and scaling startups which taught him the value of community.
During the spring of 2021, following the sale of StartNow Pittsburgh, John began to look for ways to take his operations knowledge to the next level and discovered the Coho Chief of Staff fellowship. Without hesitating, John applied to be a part of the 2nd cohort.
Although his discovery of the Coho Chief of staff fellowship came first, his next opportunity wasn’t far behind. Only about a month after applying, John landed his next opportunity and was hired as a Chief of Staff for an AgTech robotics company called Four Growers based in his hometown. The stars had aligned, and within 30 days, John kicked off his next career move and joined Coho that would take his skills to new heights.
Before he knew it, John was drinking from a fire hose in his new role with Four Growers. The company was founded on a mission to provide healthy, affordable, local produce by reducing the costs of greenhouse growers through robotics. John was excited; this wasn’t just a startup that was tied to the attention economy. It was a startup trying to solve a real problem in the real world.
Its first product, a tomato harvesting system for greenhouses, was getting ready to move from R&D into a commercialization phase. As employee #6, he was in charge of non-product-related departments (operations, HR, finance, marketing, and special projects). John had to become a swiss army knife—whatever fire popped up on a given day, it was his job to put it out.
On top of that, John was still trying to navigate the ebbs and flows of being a Chief of Staff - a role he had only been aware of for a year prior to beginning his time with Four Growers. The programming provided by the CoS fellowship helped remove the mystery of the role as both speakers, and fellow cohort members shared their experiences and as John navigated the onboarding process. It helped him understand the constant context-switching that the Chief of Staff role requires, how to batch tasks, and how to build repeatable processes that can scale with the company.
With a new job secured and with the support of a community of like-minded peers, the excitement surrounding John’s career was something to behold. The community that Coho offered was unlike any other group he had been a part of. The diversity in participants, industries, and skill sets was noticeable, and the cross-collaboration between everyone showcased a considerable value add from day one.
“After struggling to meet new people during the pandemic, the Coho community was a breath of fresh air to my business network and my career. The fellowship opened my eyes to the value of putting myself in the middle of new experiences and taking chances with professionals looking to achieve similar things. It wasn’t long before I started to reach out and have one-on-one virtual coffee chats with fellow participants. Out of the 80 participating fellows, I purposely sought out conversations with at least 30+.”
As the Chief of Staff for a seed-funded startup, there are endless challenges to solve and processes to improve. From minor responsibilities such as day-to-day facility operations to developing a recruiting strategy to double the team, context switching is a required skill set. The Coho fellows was there for help whenever a new challenge arose.
“One of my main targets within the more extensive set of responsibilities was to lead and help navigate our efforts to double our staff (going from six to twelve) within the first six months of starting at the company. In addition, I had to review & solidify HR processes around an expanding team - which included employee reviews, handbook modifications, and strategies to recruit engineering talent. If I dealt with a situation I had little or no experience in, I knew I could lean on the Coho community to gain insight into how others approached these same issues.
Need help with what you’re facing at work? Post it for the community to review.
Regardless of the question, you’re bound to get eight to ten solid answers in 48 hours from the community. It was extremely beneficial.”
But the helpfulness of the community didn’t stop at Q&A. Often, the Chief of Staff role can be lonely - balancing being seen as a leader by employees while being trusted with a large amount of sensitive information.
“Being in this role is unique. And while it does come with many positives, I’ve often felt that I’m sitting on my own island from time to time. There isn’t anyone to turn to within your company for answers - leadership expects you to figure it out while the employees look to you for answers. Drawing and connecting with other professionals outside your company was invaluable.”
For example, John was tasked to develop a new standard for employee reviews, especially one that would scale with the company. Employee feedback is helpful for any organization but critical for a startup. Through the Coho community, John was able to review templates and standards from other members. They provided how they approached similar tasks and what metrics they relied on. The end deliverable was on John to create, but the data and insights he was able to gather through Coho made the challenge easier.
With any of the Coho fellowships, the cohorts are tailored for all professionals. However, the one thing that every participant is committed to is the pursuit of lifelong learning. John noticed that every fellow Chief of Staff cohort member always sought ways to improve their work performance while accelerating their careers. If you come to the fellowship with a strong work ethic and desire to learn, you’ll thrive in the environment.
“Coho is a big melting pot of different ways to do things, approaches, and strategies. Everyone comes from diverse backgrounds, companies, and industries. You must be open to adopting distinct ways people do things and see if it applies to your situation. It could lead to you being 5%, 10%, or even 20% better at what you do. There’s a lot of knowledge and expertise that you can benefit from if you come to it with an open mind.”
While John found numerous opportunities to learn from the fellowship, he also felt a need to give back. The generosity within the community encourages reciprocity amongst its members. And to be an outstanding participant, you need to give back in addition to receiving.
“It’s not about take, take, take. It’s about: How can I contribute to the group? What information can I share? What templates can I share? Or even being there for someone when they’re having a bad day. Is there a way that I can listen or provide guidance? I’m a big believer in investing in the group. If someone wants to invest in Coho, I think the best way to get a lot out of the fellowship is to give, give, give.”
John’s commitment to that led him down the path of sharing his experiences and knowledge with others. His previous roles as a COO allowed him to lead a presentation around the potential transition from CoS to COO, a change that many CoS want to make but find challenging to navigate. John discussed how to approach the leap to COO, what is often required, and how to determine if it is the right move for you. He looked at the frameworks to best position yourself for the role, what you’ll encounter along the way, and how the transition naturally ties into what you are already doing as a CoS. He also co-led another presentation around demystifying finances for non-financial Chief of Staffs, which covered how-to dive into reading financial statements, forecasting, understanding revenue, and figuring out costs.
Preparing for those presentations and answering people’s questions forced him to refine his understanding of the material - which often led to a win-win situation for John and those listening in. But it didn’t stop there. During the fellowship, John often found himself in smaller conversations helping other fellows navigate tricky leadership situations and even helping one fellow strategize around asking for a $20,000 raise.
The Coho Chief of Staff fellowship was helpful to John’s skillset and had an immediate positive ROI. John found more than $7,000 in consulting work through the Coho network, more than offsetting the cost John paid for out of pocket.
“The Coho Chief of Staff fellowship has been a constant blessing over the last year. Within the first few months, you have to build it into your life as if you took on a 2nd job, but the asynchronous nature of it all makes it easy. I would highly recommend anyone considering joining to speak with current fellows and get a sense of the possibilities.”