I attended two offsites in the last two weeks – both great in terms of seeing people in person.  Interesting how differently they handled COVID protocols, although they were different groups with different vibes.

One was a CEO conference for one of my VC’s portfolios.  There was a huge emphasis in all the pre-conference comms about COVID.  And lots of testing.  We all got mailed a very sophisticated in-house PCR test ahead of time to take and photograph/upload, complete with chemical reagents and some kind of centrifuge.  Then those of us who flew in for the event had to do an on-site rapid test before entering the opening reception and even had a side room to sit in for 15 minutes while we were waiting for the rest results.  Once in the room, everyone was super awkward at the beginning.  Should I wear a mask?  Do I shake hands?  Hug?  Wave?  Bump elbows?  But once we got into the flow of the meeting, people were more relaxed and interactive…even some close talking.

The other was my company, Bolster – our first ever “all hands” meeting in person (we started the company just 18 months ago and have people in multiple locations).  The COVID topic was almost nonexistent.  We only have 25 people, and everyone is vaccinated, no one is immuno-compromised, and the couple of people with young and unvaccinated children are very much not on lockdown (that could be more regional – I see that more in NY than in CA).  We simply asked people to get tested before they come on the honor system and then told people when we got there that people should do whatever they were comfortable doing in terms of masks and contact, no judgment.  There was no awkwardness that I could tell at all.

In terms of the meetings themselves, both were great – it was fantastic to be live with other humans!  While there is a lot to be said for the efficiency of 15 and 30 minute meetings on Zoom, that pattern of work can’t be 100% of your year.  It doesn’t allow for serendipitous hallway interactions or highly effective design collaboration like whiteboards and post-its do.

What neither group nailed was blending people actually at the offsite with a few people who didn’t want to, or couldn’t, attend in person.  That’s got to become the norm for offsites going forward, for sure.  Videoconference software or hardware/software combinations need to get better at supporting the hybrid environment for sure, but so do meeting facilitators.

All in, while I’m looking forward to traveling less in the future, there’s much to be said for meeting in person from time to time and figuring out how to optimize that time.

As I mentioned in a previous post, I write a column for The Magill Report, the new venture by Ken Magill, previously of Direct magazine and even more previously DMNews. I share the column with my colleagues Jack Sinclair and George Bilbrey and we cover how to approach the business of email marketing, thoughts on the future of email and other digital technologies, and more general articles on company-building in the online industry – all from the perspective of an entrepreneur. I recently posted George’s column on Staying Innovative as Your Business Grows (Part One). Below is a re-post of George’s second part of that column from this week, which I think my OnlyOnce readers will enjoy.

Guest Post: Staying Innovative as Your Business Grows (Part Two)

By George Bilbrey
Last month, as part of the Online Entrepreneur column, I shared some of Return Path’s organizational techniques we use to stay innovative as we grow. In this article, I’ll talk about the process we’re using in our product management-and-development teams to stay innovative.

The Innovation Process at Return Path
As we grew bigger, we decided to formalize our process for bringing new products to market. In our early days we brought a lot of new products to market with less formal process but also with more limited resources. We did well innovating one product at a time without that kind of process largely because we had a group of experienced team members. As the team grew, we knew we had to be more systematic about how we innovated to get less experienced product managers and developers up to speed and having an impact quickly.

We had a few key objectives when designing the process:

• We wanted to fail fast – We had a lot of new product ideas that seemed like good ones. We wanted a process that allowed us to quickly determine which ideas were actually good.

• We wanted to get substantial customer feedback into the process early – We’d always involved clients in new product decisions, but generally only at the “concept” phase. So we’d ask something like “Would you like it if we could do this thing for you?” which often elicited a “Sure, sounds cool.” And then we’d go off and build it. We wanted a process that instead would let us get feedback on features, function, service levels and pricing as we were going so we could modify and adjust what we were building based on that iterative feedback.

• We wanted to make sure we could sell what we could build before we spent a lot of time building it – We’d had a few “build it and they will come” projects in the past where the customers didn’t come. This is where the ongoing feedback was crucial.

The Process
We stole a lot of our process from some of the leading thinkers in the “Lean Startup” space – particularly Gary Blanks’ Four Steps to the Epiphany and Randy Komisar’s Getting to Plan B. The still-evolving process we developed has four stages:

Stage 1: Confirm Need

Key Elements

• Understand economic value and size of problem through intense client Interaction
• Briefly define the size of opportunity and rough feasibility estimate – maybe with basic mockups
• Key Question: Is the need valid? If yes, go on. If no, abandon project or re-work the value proposition.

Stage 2: Develop Concept

Key Elements

• Create a high fidelity prototype of product and have clients review both concept and pricing model
• Where applicable, use data analysis to test feasibility of product concept
• Draft a more detailed estimate of effort and attractiveness, basically a business model
• Key Question: Is the concept Valid? If yes, go on. If no, abandon project.

Stage 3: Pilot

Key Elements

• Build “minimum viable product” and sell (or free beta test with agreed to post beta price) with intense client interaction and feedback
• Develop a marketing and sales approach
• Develop a support approach
• Update the business model with incremental investment requirements
• Preparation of data for case studies
• Key Question: Is project feasible? If yes, go on. If no, abandon project or go back to an earlier stage and re-work the concept.

Stage 4: Full Development and Launch

Key Elements

• Take client feedback from Pilot and apply to General Availability product
• Create support tools required
• Create sales collateral, white papers, lead generation programs, case studies and PR plan.
• Train internal teams to sell and service.
• Update business model with incremental investment required
• Go forth and prosper

There are a several things to note about this process that we’ve found to be particularly useful:

• A high fidelity prototype is the key to getting great customer feedback – You get more quality feedback when you show them something that looks like the envisioned end product than talking to them about the concept. Our prototypes are not functional (they don’t pull from the databases that sit behind them) but are very realistic HTML mockups of most products.

• Selling the minimum viable product (MVP) is where the rubber meets the road – We have learned the most about salability and support requirements of new products by building an MVP product and trying to sell it.

• Test “What must be true?” during the “Develop Concept” and “Pilot Phases” – When you start developing a new product, you need to know the high risk things that must be true (e.g., if you’re planning to sell through a channel, the channel must be willing and able to sell). We make a list of those things that must be true and track those in weekly team meetings.

• This is a very cross functional process and should have a dedicated team – This kind of work cannot be done off the side of your desk. The team needs to be focused just on the new product.

While not without bumps, our team has found this process very successful in allowing us to stay nimble even as we become a much larger organization. As I mentioned in Part 1, our goal is really to leverage the strengths of a big company while not losing the many advantages of smaller, more flexible organizations.

Scaling Me

Two things have come up over the last couple years for me that are frustrations for me as a CEO of a high growth company.  These are both people related — an area that’s always been the cornerstone of my leadership patterns.  That probably makes them even more frustrating.

Frustration 1:  Not knowing if I can completely trust the feedback I get from deep in the organization.  I’ve always relied on direct interactions with junior staff and personal observation and data collection in order to get a feel for what’s going on.  But a couple times lately, people had been admonishing me (for the first time) when I’ve relayed feedback with comments like, “of course you heard that — you’re the CEO.”

So now the paranoid Matt kicks in a bit.  Can I actually trust the feedback I’m getting?  I think I can.  I think I’m a good judge of character and am able to read between the lines and filter comments and input and responses to questions I ask.  But maybe this gets harder as the organization grows and as personal connections to me are necessarily fewer and farther between.

Frustration 2:  Needing to be increasingly careful with what I say and how I say it.  This comes up in two different ways.  First, I want to make sure that while I’m still providing as transparent leadership as I can, that I’m not saying something that’s going to freak out a more junior staff member because they’re missing context or might misinterpret what I’m saying.  Ok, this one I can manage.

But the tougher angle on this is having unintended impact on people.  Throwing out a casual idea in a conversation with someone in the company can easily lead to a chain reaction of “Matt said” and “I need to redo my goals” conversations that aren’t what I meant.  So I’ve done some work to formalize feedback and communication loops when I have skip-level check-ins, but it’s creating more process and thought overhead for me than I’m used to.

Nothing is bad here – just signs of a growing organization – but some definite changes in how I need to behave in order to keep being a strong and successful leader.

Book Short:  Wither the Team

I have one or two more to go, which I’ll tackle in due course and am looking forward to.

Boards That Lead, by Ram Charan, Dennis Carey, and Michael Useem, was recommended to me by a CEO Coach in the Bolster network, Tim Porthouse, who said he’s been referring it to his clients alongside Startup Boards. I don’t exactly belong in the company of Ram Charan (Brad and Mahendra probably do!), so I was excited to read it. While it’s definitely the “big company” version to Startup Boards, there are some good lessons for startup CEOs and founder to take away from it.

The best part about the book as it relates to ALL boards is the framework of Partner, Take Charge, Stay out of the Way, and Monitor. You can probably lump all potential board activities into these four buckets. If you look at it that way…these are pretty logical:

• Monitor – what you’d expect any board to do
• Stay out of the Way – basic execution/operations
• Partner – strategy, goals, risk, budget, leadership talent development
• Take Charge – CEO hiring/firing, Exec compensation, Ethics, and Board Governance itself.

There was an interesting nugget in the book as well called the Central Idea that I hadn’t seen articulated quite this way before. It’s basically a statement of what the business is and how it’s going to win. It’s about a page long, 8-10 bullet points, and it includes things like mission, strategy, key goals, and key operating pillars that underlie the goals. It basically wraps up all of Lencioni’s key questions in one page with a little more meat on the bones. I like it and may adopt it. The authors put the creation of the Central Idea into the Take Charge bucket, but I’d put it squarely in the Partner bucket.

Other than that, the book is what you’d expect and does have a lot of overlap with the world of startups. Its criteria for director selection are very similar to what we use at Bolster, as is its director evaluation framework. The book has a ton of handy checklists as well, some of which are more applicable than others to startups, for example Dealing with Nonperforming Directors and Spotting a Failing CEO.

All in, a good read if you’re a student of Boards.

Stamina

A couple years ago I had breakfast with Nick Mehta, my friend who runs the incredibly exciting Gainsight.  I think at the time I had been running Return Path for 15 years, and he was probably 5 years into his journey.  He said he wanted to run his company forever, and he asked me how I had developed the stamina to keep running Return Path as long as I had.  My off the cuff answer had three points, although writing them down afterwards yielded a couple more.  For entrepreneurs who love what they do, love running and building companies for the long haul, this is an important topic.  CEOs have to change their thinking as their businesses scale, or they will self implode!  What are five things you need to get comfortable with as your business scales in order to be in it for the long haul?

Get more comfortable with not every employee being a rock star.  When you have 5, 10, or even 100 employees, you need everyone to be firing on all cylinders at all times.  More than that, you want to hire “rock stars,” people you can see growing rapidly with their jobs.  As organizations get larger, though, not only is it impossible to staff them that way, it’s not desirable either.  One of the most influential books I’ve read on hiring over the years, Topgrading (review, buy), talks about only hiring A players, but hiring three kinds of A players:  people who are excellent at the job you’re hiring them for and may never grow into a new role; people who are excellent at the job you’re hiring them for and who are likely promotable over time; and people who are excellent at the job you’re hiring them for and are executive material.  Startup CEOs tend to focus on the third kind of hire for everyone.  Scaling CEOs recognize that you need a balance of all three once you stop growing 100% year over year, or even 50%.

Get more comfortable with people quitting.  This has been a tough one for me over the years, although I developed it out of necessity first (there’s only so much you can take personally!), with a philosophy to follow.  I used to take every single employee departure personally.  You are leaving MY company?  What’s wrong with you?  What’s wrong with me or the company?  Can I make a diving catch to save you from leaving?  The reality here about why people leave companies may be 10% about how competitive the war for talent has gotten in technology.  But it’s also 40% from each of two other factors.  First, it’s 40% that, as your organization grows and scales, it may not be the right environment for any given employee any more. Our first employee resigned because we had “gotten too big” when we had about 25 employees.  That happens a bit more these days!  But different people find a sweet spot in different sizes of company.  Second, it’s 40% that sometimes the right next step for someone to take in their career isn’t on offer at your company.  You may not have the right job for the person’s career trajectory if it’s already filled, with the incumbent unlikely to leave.  You may not have the right job for the person’s career trajectory at all if it’s highly specialized.  Or for employees earlier in their careers, it may just be valuable for them to work at another company so they can see the differences between two different types of workplace.

Get more comfortable with a whole bunch of entry level, younger employees who may be great people but won’t necessarily be your friends.  I started Return Path in my late 20s, and I was right at our average age.  It felt like everyone in the company was a peer in that sense, and that I could be friends with all of them.  Now I’m in my (still) mid-40s and am well beyond our average age, despite my high level of energy and of course my youthful appearance.  There was a time several years ago where I’d say things to myself or to someone on my team like “how come no one wants to hang out with me after work any more,” or “wow do I feel out of place at this happy hour – it’s really loud here.”  That’s all ok and normal.  Participate in office social events whenever you want to and as much as you can, but don’t expect to be the last man or woman standing at the end of the evening, and don’t expect that everyone in the room will want to have a drink with you.  No matter how approachable and informal you are, you’re still the CEO, and that office and title are bound to intimidate some people.

Get more comfortable with shifts in culture and differentiate them in your mind from shifts in values.  I wrote a lot about this a couple years ago in The Difference Between Culture and Values . To paraphrase from that post, an organization’s values shouldn’t change over time, but its culture – the expression of those values – necessarily changes with the passage of time and the growth of the company.  The most clear example I can come up with is about the value of transparency and the use case of firing someone.  When you have 10 employees, you can probably just explain to everyone why you fired Joe.  When you have 100 employees, it’s not a great idea to tell everyone why you fired Joe, although you might be ok if everyone finds out.  When you have 1,000 employees, telling everyone why you fired Joe invites a lawsuit from Joe and an expensive settlement on your part, although it’s probably ok and important if Joe’s team or key stakeholders comes to understand what happened.  Does that evolution mean you aren’t being true to your value of transparency?  No.  It just means that WHERE and HOW you are transparent needs to evolve as the company evolves.

• Get more comfortable with process.  This doesn’t mean you have to turn your nimble startup into a bureaucracy.  But a certain amount of process (more over time as the company scales) is a critical enabler of larger groups of people not only getting things done but getting the right things done, and it’s a critical enabler of the company’s financial health.  At some point, you and your CFO can’t go into a room for a day and do the annual budget by yourselves any more.  But you also can’t let each executive set a budget and just add them together.  At some point, you can’t approve every hire yourself.  But you also can’t let people hire whoever they want, and you can’t let some other single person approve all new hires either, since no one really has the cross-company view that you and maybe a couple of other senior executives has.  At some point, the expense policy of “use your best judgment and spend the company’s money as if it was your own” has to fit inside department T&E budgets, or it’s possible that everyone’s individual best judgments won’t be globally optimal and will cause you to miss your numbers.  Allow process to develop organically.  Be appropriately skeptical of things that smell like bureaucracy and challenge them, but don’t disallow them categorically.  Hire people who understand more sophisticated business process, but don’t let them run amok and make sure they are thoughtful about how and where they introduce process to the organization.

I bet there are 50 things that should be on this list, not 5.  Any others out there to share?

New People Electrify the Organization

We had a good year in 2009, but it was tough.  Whose wasn’t?  Sales were harder to come by, more existing customers left or asked for price relief than usual, and bills were hard to collect.  Worse than that, internally a lot of people were in a funk all year.  Someone on our team started calling it “corporate ennui.”  Even though our business was strong overall and we didn’t do any layoffs or salary cuts, I think people had a hard time looking around them, seeing friends and relatives losing their jobs en masse, and feeling happy and secure.  And as a company, we were doing well and growing the top line, but we froze a lot of new projects and were in a bit of a defensive posture all year.

What a difference a year makes.  This year, still not perfect, is going much better for us.  Business conditions are loosening up, and many of our clients have turned the corner.  Financially, we’re stronger than ever.  And most important, the mood in the company is great.  I think there are a bunch of reasons for that – we’re investing more, we’re doing a ton of new innovation, people have travel budgets again, and people see our clients and their own friends in better financial positions.

But by far, I think the most impactful change to the organizational mood we’re seeing is a direct result of one thing:  hiring.  We are adding a lot of new people this year – probably 60 over the course of the year on top of the 150 we had at the beginning of the year.  And my observation, no matter which office of ours I visit, is that the new people are electrifying the organization.  Part of that is that new people come in fresh and excited (perhaps particularly excited to have a new job in this environment).  Part of it is that new people are often pleasantly surprised by our culture and working environment.  Part of it is that new people come in and add capacity to the team, which enables everyone to work on more new things.  And part of it is that every new person that comes in needs mentoring by the old timers, which gives the existing staff reminders and extra reason to be psyched about what they’re doing, and what the company’s all about.

Whether it’s one of these things or all of them, I’m not sure I care.  I’m just happy the last 18 months are over.  The world is a brighter place, and so is Return Path.  And to all of our new people (recent and future), welcome…thanks for reinvigorating the organization!

As I mentioned in last week’s post, I’m rebooting my work self this year, and this quarter in particular.  One of the things I am doing is getting back to basics on a few fronts.

Over the holiday break, as I was contemplating a reboot, I emailed a handful of people with whom I’ve worked closely over the years, but for the most part people with whom I no longer work day in day out, to ask them a few questions.  The questions were fairly backward looking:

1.       When I was at my best, what were my personal habits or routines that stand out in your mind?

2.       When I was at my best, what were my work behaviors or routines that stand out in your mind?

3.       When our EC was at its best, what were the team dynamics that caused it to function so well?

I got some wonderful responses, including one which productively challenged the premise of asking backward-looking questions as I was trying to reboot for the future.  (The answer is that this was one of several things I was doing as part of Rebooting, not the only thing, and historical perspective is one of many useful tools.)

Although the question clearly led itself to this, the common theme across all the answers was “back to basics.”  Part of evolving myself as a CEO as the company has grown over the years has been stopping doing particular things and starting others intentionally.  I try to do that at least once a year.  But what this particular exercise taught me is that, like the proverbial boiled frog, there were a slew of small and medium-sized things that I’ve stopped doing over the years unintentionally that are positive and productive habits that I miss.  I have a long list of these items, and I probably won’t want or need to get to all of them.  But there are a few that I think are critical to my success for various reasons.  Some of the more noteworthy ones are:

• Blogging, which I mentioned in last week’s post as an important way for me to reflect and crystallize my thinking on specific topics
• Ensuring that I have enough open time on my calendar to breathe, think, keep current with things.  When every minute of every day is scheduled, I am working harder, but not smarter
• Be more engaged with people at the office.  This relates to having open time on the calendar.  Yesterday I sat in our kitchen area and had a quick lunch with a handful of colleagues who I don’t normally interact with.  It was such a nice break from my routine of “sit at desk, order food in” or “important business lunch,” I got to clear my head a little bit, and I got to know a couple things about a couple people in the office that I didn’t previously know
• Get closer to the front lines internally.  Although I’ve maintained good external contacts as the company has grown with key clients and partners, our multi-business-unit structure has had me too disconnected from Sales and Engineering/Product in particular.  This one may take a couple months to enact, but I need to get closer to the action internally to truly understand what’s going on in the business
• Get back to a rigorous use of a single Operating System.  I’ve written a lot about this over the years, but having a David-Allen style, single place where I track all critical to do’s for me and for my team has always been bedrock for me.  I’ve been experimenting with some different ways of doing this over the last couple years, which has led to a breakdown in Allen’s main principle of “put it all in one place” – so I am going to work on fixing that
• Reading – while I have been consistently and systematically working my way through American history and Presidential biographies books over the years, I’ve almost entirely stopped reading other books for lack of time.  A well-balanced reading diet is critical for me.  So I’m working in some other books now from the other genres I love – humor (Martini Wonderland is awesome), architecture (see last week’s post on The Fountainhead), current events (I’m in the middle of Michael Lewis’ The Undoing Project and next up is Tom Friedman’s Thank You For Being Late), and business books (about to start Kotter’s A Sense of Urgency)
• Like reading, doing something creative and unrelated to work has always been an important part of keeping my brain fresh.  Coaching little league has helped a lot.  But I need to add something that’s more purely creative.  I am still deciding between taking guitar lessons (I halfway know how to play) and sculpting lessons (I don’t know a thing about it)

That’s it for now.  There are other basics that I never let lapse (for example, exercise).  But the common theme of the above, I realize now that I am writing it all out, isn’t only “back to basics.”  It’s about creating time and space for me to be fresh and exercise different muscles instead of grinding it out all day, every day.  And that’s well worth the few minutes it took me and my friends to work up this list!

Hopefully I’ll have more to say on the general topic of rebooting in another week or two as January craziness sets in with our annual kickoff meetings around the world.

The Best Laid Plans, Part III

Once you’ve finished the Input Phase and the Analysis Phase of producing your strategic plan, you’re ready for the final Output Phase, which goes something like this:

Vision articulation.  Get it right for yourself first.  You should be able to answer “where do we want to be in three years?” in 25 words or less.

Roadmap from today.  Make sure to lay out clearly what things need to happen to get from where you are today to where you want to be.  The sooner-in stuff needs to be much clearer than the further out stuff.

Resource Requirements.  Identify the things you will need to get there, and the timing of those needs – More people?  More marketing money?  A new partner?

Financials.  Lay them out at a high level on an annual basis, on a more detailed level for the upcoming year.

Packaging.  Create a compelling presentation (Powerpoint, Word, or in your case, maybe something more creative) that is crisp and inspiring.

Pre-selling.  Run through it – or a couple of the central elements of it – with one or two key people first to get their buy-in.

Selling.  Do your roadshow – hit all key constituents with the message in one way or another (could be different forms, depending on who).

The best thing to keep in mind is that there is no perfect process, and there’s never a “right answer” to strategy — at least not without the benefit of hindsight!

People have asked me what the time allocation and elapsed time should or can be for this process.  While again, there’s no right answer, I typically find that the process needs at least a full quarter to get right, sometimes longer depending on how many inputs you are tracking down and how hard they are to track down; how fanatical you are about the details of the end product; and whether this is a refresh of an existing strategy or something where you’re starting from a cleaner sheet of paper.  In terms of time allocation, if you are leading the process and doing a lot of the work yourself, I would expect to dedicate at least 25% of your time to it, maybe more in peak weeks.  It’s well worth the investment.

I’ve published two editions of Startup CEO, a sequel called Startup CXO, and am a co-author on the second edition of Startup Boards. We also just (2025) published mini-book versions of Startup CXO specifically for five individual functions, Startup CFO, Startup CRO, Startup CMO, Startup CPO, and Startup CTO.

You’re only a startup CEO once. Do it well with Startup CEO, a “master class in building a business.”

—Dick Costolo, Partner at 01A (Former CEO, Twitter)

Being a startup CEO is a job like no other: it’s difficult, risky, stressful, lonely, and often learned through trial and error. As a startup CEO seeing things for the first time, you’re likely to make mistakes, fail, get things wrong, and feel like you don’t have any control over outcomes.

As a Startup CEO myself, I share my experience, mistakes, and lessons learned as I guided Return Path from a handful of employees and no revenues to over $100 million in revenues and 500 employees.

Startup CEO is not a memoir of Return Path’s 20-year journey but a CEO-focused book that provides first-time CEOs with advice, tools, and approaches for the situations that startup CEOs will face.

You’ll learn:

How to tell your story to new hires, investors, and customers for greater alignment How to create a values-based culture for speed and engagement How to create business and personal operating systems so that you can balance your life and grow your company at the same time How to develop, lead, and leverage your board of directors for greater impact How to ensure that your company is bought, not sold, when you exit

Startup CEO is the field guide every CEO needs throughout the growth of their company and the one I wish I had.

“Startup CXO is an amazing resource for CEOs but also for functional leaders and professionals at any stage of their career.”

– Scott Dorsey, Managing Partner, High Alpha (Former CEO, ExactTarget)

One of the greatest challenges for startup teams is scaling because usually there’s not a blueprint to follow, people are learning their function as they go, and everyone is wearing multiple hats. There can be lots of trial and error, lots of missteps, and lots of valuable time and money squandered as companies scale. My team and I understand the scaling challenges—we’ve been there, and it took us nearly 20 years to scale and achieve a successful exit. Along the way we learned what worked and what didn’t work, and we share these lessons learned in Startup CXO.

Unlike other business books, Startup CXO is designed to help each functional leader understand how their function scales, what to anticipate as they scale, and what things to avoid. Beyond providing function-specific advice, tools, and tactics, Startup CXO is a resource for each team member to learn about the other functions, understand other functional challenges, and get greater clarity on how to collaborate effectively with the other functional leads.

CEOs, Board members, and investors have a book they can consult to pinpoint areas of weakness and learn how to turn those into strengths. Startup CXO has in-depth chapters covering the nine most common functions in startups: finance, people, marketing, sales, customers, business development, product, operations, and privacy. Each functional section has a “CEO to CEO Advice” summary from me on what great looks like for that CXO, signs your CXO isn’t scaling, and how to engage with your CXO.

Startup CXO also has a section on the future of executive work, fractional and interim roles. Written by leading practitioners in the newly emergent fractional executive world, each function is covered with useful tips on how to be a successful fractional executive as well as what to look for and how to manage fractional executives.

A comprehensive guide on creating, growing, and leveraging a board of directors written for CEOs, board members, and people seeking board roles.

The first time many founders see the inside of a board room is when they step in to lead their board. But how do boards work? How should they be structured, managed, and leveraged so that startups can grow, avoid pitfalls, and get the best out of their boards? Authors Brad Feld, Mahendra Ramsinghani, and Matt Blumberg have collectively served on hundreds of startup and scaleup boards over the past 30 years, attended thousands of board meetings, encountered multiple personalities and situations, and seen the good, bad, and ugly of boards.

In Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, the authors provide seasoned advice and guidance to CEOs, board members, investors, and anyone aspiring to serve on a board. This comprehensive book covers a wide range of topics with relevant tips, tactics, and best practices, including:

• Board fundamentals such as the board’s purpose, legal characteristics, and roles and functions of board members;
• Creating a board including size, composition, roles of VCs and independent directors, what to look for in a director, and how to recruit directors;
• Compensating, onboarding, removing directors, and suggestions on building a diverse board;
• Preparing for and running board meetings;
• The board’s role in transactions including selling a company, buying a company, going public, and going out of business;
• Advice for independent and aspiring directors.

Startup Boards draws on the authors’ experience and includes stories from board members, startup founders, executives, and investors. Any CEO, board member, investor, or executive interested in creating an active, involved, and engaged board should read this book—and keep it handy for reference.

Five new mini-books from Startup CXO, but with new bonus material and an obvious focus on each specific functional area.

Each book has several topics in common – chapters on the nature of an executive’s role, how a fractional person works in that role, how the role works with the leadership team, how to hire that role, how the role works in the beginning of a startup’s life, how the role scales over time, and CEO:CEO advice about managing the role.

In Startup CTO (Technology and Product), the role-specific topics Shawn Nussbaum talks about are The Product Development Leaders, Product Development Culture, Technical Strategy, Proportional Engineering Investment and Managing Technical Debt, Shifting to a New Development Culture, Starting Things, Hiring Product Development Team Members, Increasing the Funnel and Building Diverse Teams, Retaining and Career Pathing People, Hiring and Growing Leaders, Organizing Collaborating with and Motivating Effective Teams, Due Diligence and Lessons Learned from a Sale Process, Selling Your Company, Preparation, and Selling Your Company/Telling the Story.

In Startup CMO, the role-specific topics Nick Badgett and Holly Enneking talk about are Generating Demand for Sales, Supporting the Company’s Culture, Breaking Down Marketing’s Functions, Events, Content & Communication, Product Marketing, Marketing Operations, Sales Development, and Building a Marketing Machine.

In Startup CFO, the role-specific topics Jack Sinclair talks about are Laying the CFO Foundation, Fundraising, Size of Opportunity, Financial Plan, Unit Economics and KPIs, Investor Ecosystem Research, Pricing and Valuation, Due Diligence and Corporate Documentation, Using External Counsel, Operational Accounting, Treasury and Cash Management, Building an In-House Accounting Team, International Operations, Strategic Finance, High Impact Areas for the Startup CFO as Partner, Board and Shareholder Management, Equity, and M&A.

In Startup CRO, the role-specific topics Anita Absey talks about are Hiring the Right People, Profile of Successful Sales People, Compensation, Pipeline, Scaling the Sales Organization, Sales Culture, Sales Process and Methodology, Sales Operating System, Marketing Alignment, Market Assessment & Alignment, Channels, Geographic Expansion, and Packaging & Pricing.

In Startup CPO (HR/People), the role-specific topics Cathy Hawley talks about are Values and Culture, Diversity Equity and Inclusion, Building Your Team, Organizational Design and Operating Systems, Team Development, Leadership Development, Talent and Performance Management, Career Pathing, Role Specific Learning and Development, Employee Engagement, Rewards and Recognition, Reductions in Force, Recruiting, Onboarding, Compensation, People Operations, and Systems.

From Founder/Builder to Manager/Leader

After I spoke at the Startup2Startup event last month, one of the people who sat with me at dinner emailed me and asked:

I was curious–how did you make the transition from CEO of a startup to manager of a medium-sized business? I’m great at just doing the work myself and interacting with clients, and it’s easy for me to delegate tasks, but it’s hard to have the vision and ability to develop my two employees into greater capacity…

I’d be interested in reading a blog post on what helped you make that transition from founder/builder to manager/leader

It feels like the answer to this question is about a mile long, but I thought I’d at least start with five suggestions.

1. Hire Up!  The place where I see most founders fumble the transition is in not hiring the best people for the critical roles in the organization.  Sometimes this is for cash flow reasons, but more often it is either due to subconscious fear (“will I still be able to control the organization if this person is in it?”) or due to bravado (“I can do engineering way better than that guy”).  Lose that attitude and hire up for key positions.  Even if you COULD do every role better than anyone you’d ever hire, you only have so many hours in the day.
2. Learn the magic of delegation and empowerment.  You can never get as much work done on your own as you can if you get work done THROUGH others.  Get comfortable delegating work by setting clear expectations up front in terms of timing and quality of deliverables and giving your high level input.  And never be a bottleneck.  If people are waiting on you for decisions or comments, that means they’re not working…or at least that they’re not working on the highest value or most urgent things they could be working on.
3. Don’t fear some elements of larger organizations.  Larger organizations require some process so they don’t fall apart.  Make sure you pick your battles and accept that some changes, even if they feel bureaucratic, are critical to ensure success going forward.  I still get a queasy feeling in my stomach half of the times I see a new form or procedure or a suggestion from a lawyer, but as long as they are lightweight and constantly reviewed to make sure they’re having their intended impact AND ONLY their intended impact, some are inevitable.
4. At the same time, don’t lose the founder/builder mentality.  Your company may have grown larger, but if you’re still running it, people will naturally look to you and other founders for much of the energy, vision, and drive in the business.  You will also likely be more inclined to be scrappy and entrepreneurial, which are good traits for any business.  Don’t lose those qualities, even as you modify them or add others.
5. Look to the outside for help.  In my case, I’ve consistently done three things over the years to learn from others and to prevent myopia.  First, I have worked on and off with a fantastic executive coach, Marc Maltz from Triad Group. Second, I have always had one or two “CEO mentors,” e.g., guys who have built larger businesses than Return Path, on my Board, at all times, as resources.  Finally, I do a lot of CEO peer networking, some informal (breakfasts, drinks meetings), and some more formal (a CEO Forum group that I established) to make sure I’m consistently sharing information and best practices with others in comparable situations.

Any other entrepreneurs who have made the leap have other advice to offer?