Category Archives: CEO

Whose Company Is It Anyway? Differences between Founders and Hired CEOs.

Over the years I’ve noticed how different CEOs take different degrees of ownership and accountability when it comes to the board of directors.  For example, once, after a long debate where the board unanimously approved a budget contingent on reducing proposed R&D spending from $12M to $10M, I overhead the founder/CEO telling the head of R&D to “spend $12M anyway” literally as we walked out of the meeting [1].  That would be one extreme.

On the other, I’ve seen too-many CEOs treat the board as their boss, seemingly unwilling to truly lead the company, or perhaps hoping to earn a get out of jail free card if good execution of a chosen plan nevertheless fails.

This all relates to a core Kellblog theme of ownership — who owns what — that I’ve explored in some of my most popular posts:

Let’s now apply the same kind of thinking to the job of the CEO.  Startup CEOs generally fall into one of two categories and the category is likely to predict how they will approach the ownership issue.

Founder CEOs:  It’s My Company

Founders think it’s their company, well, because it is.  Whether they currently own more than 80% or less than 5% of the stock, whether they currently even work there anymore or not, it’s their company and always will be.  CEOs will come and go along a startup’s journey, but there is only one founder [2].  The founder started the company and made a big cultural imprint on it.  Nothing can take that away.

However, as soon as a founder/CEO raises venture capital (VC) they have decided to take investing partners along on the journey.  The best VC investors view their relationship with the founder as a partnership:  it’s the founder’s company, we are investing to partner with the founder, and our primary job is to advise and support the founder so as to help maximize the outcome.

However, VC investors are material shareholders, typically negotiate the contractual right to sit on the board of directors, and have certain governance and fiduciary duties as a part of sitting on the board.  (Those fiduciary duties, by the way, get complicated fast as VC board members also have fiduciary duties to their funds as well [3].)

Most of the time, in my experience, VCs run in advice/support mode, but if a company starts to have continual performance problems, is considering a new financing, or evaluating potential exit opportunities (e.g., M&A), founders can get a quick (and sometimes stark) reminder of the “second hat” that their VCs wear.

While it’s always spiritually the founder’s company, it’s only really and totally the founder’s company if they’ve never raised money [4].  Thankfully, most founder/CEOs don’t need to be reminded of that.  However, some do [5].

Hired CEOs:  It’s the Board’s Company vs. It’s My Company to Run

You become a hired CEO primarily through one path — climbing the corporate ladder at a large tech company [5a], reaching the GM or CXO level, and then deciding to branch out.  While virtually all hired CEOs have been large-tech CXOs or GMs, not all large-tech CXOs or GMs are wired to be successful as CEOs in the more frenetic world of startups.

Regardless of whether they should take the plunge, the problem that CEOs sometimes face is fighting against decades of training in climbing the corporate ladder.  Ladder-climbing wires you with three key priorities [6]:

  • Always make the boss look good
  • Never surprise the boss
  • Build strong relationships with influential peers

The problem?  When you’re CEO of a startup there is no boss and there are no peers.  Yes, there is a board of directors but the board/CEO relationship is not the same as the manager/employee relationship with which corporate execs are so familiar.

Yes, boards provide strategic and financial input, support, guidance, help with recruiting, and occasionally help with sales, but boards don’t run companies.  CEOs do.  And to repeat one of my favorite CEO quotes from Sequoia founder Don Valentine:  “I am 100% behind my CEOs up until the day I fire them” [7].

The challenge for hired CEOs is for them to understand:  it’s not my company in the sense that I founded it, but it is my company to run.  It’s not the board’s company to run and the board is not my manager.  The board is my board, and it’s not at all the same relationship as manager/employee.
Because this is somewhat conceptual, let’s provide an example to make this concrete.

“It’s My Company” Thinking “It’s the Board’s Company” Thinking
Based on what is happening in the market and our models we think it’s best to shoot for growth of X% and EBITDA margin of Y% How much do you want us to grow next year and at what EBITDA margin?
We believe we need to focus on a vertical and we think Pharma is the best choice. We were thinking that maybe we could focus more on a vertical, what do you folks think?
We think we should hold off doing channels until we’ve debugged the sales model. You told us to do channels so we signed up 17 partners but no one is actually selling anything.  Maybe it wasn’t a great idea.
Pattern:  we think we should do X and here’s why.  Please challenge it. Pattern:  we are here to do what you want, so what do you want us to do?  

CEOs need to remember that:

  • The management team spends 50-60 hours/week working at the company.  The board might spend that same amount of time in a year [8].  The team is much, much closer to the business and in the best position to evaluate options.
  • Even if they don’t always sound that way, the board wants the CEO to lead.  The scariest thing a new CEO can say is “it looks like you guys had a bad quarter” [9]. The second scariest thing is “looks like we had a bad quarter, what do you want us to do about it?”  Instead, they want to hear, “we had a bad quarter and here’s our plan to get things back on track.  Please give us frank feedback on that plan because we want the best plan possible and we want it to work [10].”
  • The CEO’s job is not to execute the board’s plan.  The CEO’s job is to work with the team to create the plan, get board approval of it, and then execute.  If the plan doesn’t work, the CEO doesn’t get to say “but you approved it, so you can’t fire me.” The job was to both make and execute the plan.

Finally, there are certain risk factors that can increase the chance a hired CEO will adopt the wrong type of thinking:

  • PE-backed firms.  In most venture-backed firms, a hired CEO will find a board consisting of several different venture capital partners, each with their own opinion.  Even though most venture boards do end up with an Alpha member [11], it’s still hard for the CEO to get confused and think of the Alpha member as the boss.  In a PE-backed firm, however, the board may consist of a single investing partner from the one firm who owns the company, perhaps accompanied by a few more junior staff.  In this case, it’s fairly easy for the CEO to revert to CXO-mode and treat that board member as “the boss” as opposed to “the board.”  While PE firms are more active managers who often come with playbooks and best practices consultants, they still want the CEO to be the CEO and not the EVP of Company.
  • First-time CEOs.  Veteran CEOs have more time to learn and understand the board/CEO relationship.  First-timers, fresh from climbing the corporate ladder, sometimes have trouble with the adjustment.

If you’re in either of the above categories or both, it’s important to ask yourself, and most probably your board, about what kind of relationship is desired.  Most of the time, in my estimation, they hired a CEO because they wanted a CEO and the more leadership you take, the more you think “my company” and not “board’s company,” the better off everyone will be.

Finally, you may also want to read this post about the board/CEO relationship which includes another of my favorite passages, on what I call the Direction Paradox.

The Direction Paradox
While discussions, challenges, advice, and questioning are always good, when boards give operational direction (i.e., “you should do X”) they risk creating a paradox for the CEO.  It’s easy when the CEO agrees with the direction and in that case the direction could have been offered as advice and still would have been heeded.
It gets hard when the CEO disagrees with the direction:

Case 1:  If the CEO follows the direction (and is correct that it was wrong), he or she will be fired for poor results.
Case 2:  If the CEO fails to follow the direction, his or her political capital account will be instantly debited (regardless of whether eventually proven right) and he or she will eventually be fired for non-alignment as the process repeats itself over time.

In case 1, the CEO will be surprised at his termination hearing.  “But, but, but … I did what you told me to do!”  “But no,” the board will reply.  “You are the CEO.  Your job is to deliver results and do what you think is right.”  And they’ll be correct in saying that.

Once caught in the paradox, weak CEOs die confused on the first hill and strong ones die frustrated on the second.

See the post for advice on how to prevent the Direction Paradox from starting.

# # # 

Notes
[1] And clearly within earshot of the directors

[2] To simplify the writing, I’ll say “one founder” meaning “one founder or equivalent” (i.e., a set of co-founders).  To the extent that this post is really about the CEO role, then it does flip back to one person, again — i.e., that co-founder (if any) who decided to take the CEO role.  This post isn’t about non-CEO co-founders, but instead about [co-]founder CEOs.

[3] See this 27-page classic (PDF) by Wilson Soncini, The Venture Capital Board Member’s Survival Guide:  Handling Conflicts While Wearing Two Hats.  It’s a must-read if you want to understand these issues.

[4] Increasingly, experienced founders (and/or those sitting on a hot enough hand) are able to raise venture capital and maintain near-total control.  Mechanisms include: a separate class of founder stock with 10x+ voting rights; control of a majority of the board seats; or protective provisions on the founder stock, such as the right to block a financing or sale of the company.  Even in such cases, however, a high-control founder still has fiduciary duties to the other shareholders.

[5] I believe incubators (and the like), by removing a lot of hard work and risk in starting a company, can inadvertently produce what I call “faux founders” who — when it comes to the business side of the company — act more like first-time hired CEOs than typical founders.  Don’t get me wrong, plenty of fine founder/CEOs come out of incubators, but I nevertheless believe that incubators increase the odds of creating a founder/CEO who can feel more like a CTO or CPO than a CEO.  That’s not to say the company won’t be successful either with that original founder or a replacement; it is to say, in my experience, that incubator founders can be different from their non-incubated counterparts.

[5a] And even better, helping to make it large while so doing.

[6] Like it or not, it’s not a bad three-part formula for climbing the corporate ladder.  And the “don’t surprise” rule still applies to boards as it does to managers.

[7] Note that any idea that the CEO might quit doesn’t seem to exist in his (or most VC’s) mind.  That’s because it’s incomprehensible because it’s a career mistake that may well make the person unemployable as CEO in a future VC-backed startup.  Who, after all, wants to hire the Captain of the Costa Concordia?  See this post, Startups CEOs and the Three Doors, for more.

[8] 6 board meetings at 4 hours = 24 hours, one hour prep per board meeting = 6 hours, 2 hours x 4 committee meetings = 8 hours, 2 hours/month on keeping up with news, updates, monthly reports = 24 hours.  Total of 62 hours/year for a committee member, less if not.  Time can vary widely and may be much higher if the board member is providing ad hoc support and/or ad hoc projects.

[9] Oh no!  The new CEO doesn’t even yet consider himself one of us!

[10] Because it’s not about ego or authorship, it’s about the best results.

[11] Often, but not always, the person who led the Series A investment.

Good CEO Habits: Proactively Update Your Board at the End of Every Quarter

I am surprised by how many startup CEOs leave the board hanging at the end of the quarter.  As a CEO my rule of thumb was that if a board member ever asked me about the quarter then I’d failed in being sufficiently proactive in communications.  In tight quarters I’d send a revised forecast about a week before the end of the quarter — hoping to pre-empt a lot of “how’s it going” pings.

And every quarter I would send an update within 24 hours of the quarter-end.  In fact, if we’d effectively closed-out all material opportunities before quarter-end, I’d send it out before the quarter was technically even over.

Why should you do this?

  • It’s a good habit.  Nobody wants to wait 3 weeks until the post-quarter board meeting to know what happened.
  • It shows discipline.  I think boards like disciplined CEOs (and CFOs) who run companies where the trains run on time.
  • It pre-empts one-of emails and phone calls.  It’s probably less work, not more, to send a quick standard end-of-quarter update that includes what you do know (e.g., bookings) but not what you don’t (e.g., expenses because accounting hasn’t closed the quarter yet).

What form should this update take?  I’d start with the board sales forecast template that I’ve already written about here.  (And I’d change Forecast to Actual and drop the Best Case and Pipeline Analysis.)

how-to-present-forecast-2.jpg

Since cash is oxygen at a start-up, I’d add a line about forecast cash flows, making sure they know the numbers are preliminary, with final numbers to follow at the upcoming board meeting.  I might add a little color on the quarter as well.

Here’s an example of a good end-of-quarter board update.

Dear Board,

Just a quick note to give you an update on the quarter at GreatCo.  We beat new ARR plan by $200K (landing at $1,700K vs. plan of $1,500K) and grew new ARR YoY by 42%.  We came in slightly under on churn ARR, landing at $175K vs. a plan of $200K.  The result is we ended the quarter $225K ahead of plan on ending ARR at $11,546K, with YoY growth of 58%.

Cash burn from operations is preliminarily forecast to be $240K ahead of plan at $2,250K and ending cash is just about at-plan of $10,125K (we were a little behind in 1Q and 2Q has caught us back up).

We had some great competitive wins against BadCo and WorseCo — I’m particularly happy to report that we won the Alpha Systems deal (that we discussed in detail at the last meeting) against BadCo for $275K.  Sarah will tell us how we turned that one around at the upcoming board meeting.

Finally, I did want to point out — given the concerns about sales hiring — that we ended the quarter with 12 quota-carrying reps (QCRs), only 1 behind plan. Sarah and Marty did a great job helping us catch almost all the way back up to plan.  That said, we’re still having trouble hiring machine-learning engineers and are nearly 5 heads behind plan to-date.  Ron and Marty will update the board on our plans to fix that at the meeting.

Overall, we feel great about the quarter and I look forward to seeing everyone in a few weeks.  Thanks, as always, for your support.

[Table with Numbers]

Cheers/Dave

# # #

The Three Marketing Books All Founder/CEOs Should Read

Few founder/CEOs come from a marketing background; most come from product, many from engineering, and some from sales, service, or consulting.  But few — ironically even in martech companies — grew up in the marketing department and consider marketing home.

When you combine this lack of experience with the the tendency that some marketing leaders and agencies have to deliberately obfuscate marketing, it’s no wonder that most founder/CEOs are somewhat uncomfortable with it.

But what’s a founder/CEO to do about this critical blind spot?  Do you let your CMO and his/her hench-agencies box you out of the marketing department?  No, you can’t.  “Marketing,” as David Packard once famously said, “is too important to be left to the marketing department.”

I recommend solving this problem in two ways:

  • One part hiring:  only hire marketing leaders who are transparent and educational, not those who try to hide behind a dark curtain of agencies, wizardry, and obfuscation.  Remember the Einstein quote:  “if you truly understand something you can explain it to a six-year old.”
  • One part self-education.  Don’t fear marketing, learn about it.  A little bit of fundamental knowledge will take you a long way and build your confidence in marketing conversations.

The problem is where to begin?  Marketing is a broad discipline and there are tens of thousands of books — most of them crap — written about it.  In this post, I’m going to list the three books that every founder/CEO should read about marketing.

I have a bias for classics here because I think founder/CEO types want foundational knowledge on which to build.  Here they are:

  • Positioning by Al Ries and Jack Trout.  Marketers frequently use the word “positioning” and after reading this classic, you’ll know exactly what they mean [1]. While it was originally published in 1981, it still reads well today.  This is all about the battle for the mind, which is the book’s subtitle.
  • Ogilvy on Advertising by David Ogilvy.  Ogilvy was the founder of marketing powerhouse agency Ogilvy and Mather and was the king of Madison Avenue back in the era of Mad Men.  Published in 1963, this book definitely shows signs of age, but the core content is timeless.  It covers everything from research to copy-writing and is probably, all in, my single favorite book on marketing. [2]
  • Crossing the Chasm by Geoffrey Moore.  The textbook classic Silicon Valley book on strategy.  Many people refer to the chasm without evidently having even read the book, so please don’t be one of them.  Published in 1991, it’s the newest of the books on my list, and happily Moore has revised it to keep the examples fresh along the way.

If I had to pick only one book, rather than suggesting original classics I’d revert to a summary, Kotler on Marketing, an overview written by Philip Kotler [3], author of one of the most popular marketing college textbooks, Marketing Management. [4]

If reading any of the above three books leaves you hungry for more (and if I were permitted to recommend just a few follow-up books), I’d offer:

  • As a follow-up to Positioning, I’d recommend The 22 Immutable Laws of Marketing also by Al Ries and Jack Trout and also written in the same accessible style.  This book would place second in the “if I only had one book to recommend” category and while less comprehensive than Kotler it is certainly far more accessible.
  • As a follow-up to Ogilvy on Advertising, and for those who want to get closer to marketing execution (e.g., reviewing content), I’d recommend The Copywriter’s Handbook by Robert Bly.  Most founder/CEOs are clear and logical writers who can get somewhat bamboozled by their marketing teams into approving gibberish copy.  This book will give you a firmer footing in having conversations about web copy, press releases, and marketing campaigns.
  • As a follow-up to Crossing the Chasm, I’d recommend Good Strategy, Bad Strategy, an excellent primer on strategy with case studies of great successes and failures and Blue Ocean Strategy, a great book on how to create uncontested market space and not simply compete in endless slug-fests against numerous competitors — which is particularly relevant in the current era of over-populated and over-funded startups. [5]

As founder/CEO you run the whole company.  But, for good reason, you might sometimes be hesitant to dive into marketing.  Moreover, some marketeers like it that way and may try to box you out of the marketing department.  Read these three books and you’ll have the tools you need to confidently engage in, and add value to, important marketing conversations at your company.

# # #

Notes

[1]  The Wikipedia entry on positioning isn’t a bad start for those in a hurry.

[2] Right from the second sentence, Ogilvy gets to the point:  “When I write an advertisement, I don’t want you to tell me that you find it ‘creative.’   I want you to find it so interesting that you buy the product.”  Love that guy.

[3] Of 4 P’s fame.  Kotler’s 4 P’s defined the marketing mix:  product, place, price, and promotion.

[4] Kotler on Marketing is deliberately not a summarized version of his classic, 700-page textbook, but alas it’s still written by someone who has produced numerous textbooks and nevertheless has a textbook feel.  It’s comprehensive but dry — especially by comparison to the others on this list.

[5] I can’t conclude any post on marketing thoughts and thinkers without a reference to one of the great marketing essays of all time, Marketing Myopia, by Theodore Levitt.  It’s old (published in 1963) and somewhat academic, but very well written and contains many pithy nuggets expressed as only Levitt could.

Video of my SaaStr 2019 Presentation: The Five Questions Startup CEOs Worry About

A few days ago, Jason Lemkin from SaaStr sent me a link to the video of my SaaStr Annual 2019 conference presentation, The Five Questions Startup CEOs Worry About. Those questions, by the way, are:

  1. When do I next raise money?
  2. Do I have the right team?
  3. How can I better manage the board?
  4. To what extent should I worry about competition?
  5. Are we focused enough?

Below is the video of the thirty-minute presentation.  The slides are available on Slideshare.

As mentioned in the presentation, I love to know what’s resonating out there, so if you ever have a moment where you think –“Hey, I just used something from Dave’s presentation!” — please let me know via Twitter or email.

Slides from My SaaStr Annual 2019 Presentation (5 Questions CEOs Struggle With)

Thanks to everyone who attended my session today at the amazing — and huge — SaaStr Annual 2019 conference in San Jose.  In this post, I’ll share the slides from my presentation, Five Questions SaaS CEOs Wrestle With (and some thoughts on how to answer them).

The folks at SaaStr recorded the session, so at some point a video of it will be available (but that probably won’t be for a while).  When it is up, I will also post it to Kellblog.

In some sense definitionally, there were two types of people in the audience:

  • CEOs, who hopefully received some fresh perspective on these age-old, never-quite-put-to-bed questions.
  • Those who work for them, who hopefully received some insights into the mind of the CEO that will help make you more valuable team members and help you advance your career.

As mentioned, please send me feedback if you have examples where something in the presentation resonated with you, you applied it in some way, and it made a positive impact on your working life.  I’d love to hear it.

Here are the slides from the presentation.

SaaStr 2019 Presentation Preview: Five Questions SaaS CEO Wrestle With

I’m super excited for the upcoming SaaStr Annual 2019 conference in San Jose from February 5th through the 7th at the San Jose Convention Center.  I hope to see you there — particularly for my session from 10:00 AM to 10:30 AM on Tuesday, February 5th.  Last year they ended up repeating my session but that won’t be possible this year as I’m flying to Europe for a board meeting later in the week — so if you want to see it live, please come by at 10:00 AM on Tuesday!

saastr 2019

I’d quibble with the subtitle, “Lessons from Host Analytics,” because it’s actually more, “Lessons From a Lifetime of Doing This Stuff,” and examples will certainly include but also span well beyond Host Analytics.  In fact, I think one thing that’s reasonably unique about my background is that I have 10+ years’ tenure in two different, key roles within an enterprise software company:

  • CEO of two startups, combined for over ten years (MarkLogic, Host Analytics).
  • CMO of two startups, combined for over ten years (BusinessObjects, Versant).

I’ve also been an independent director on the board of 4 enterprise software startups, two of which have already had outstanding exits.  And I just sold a SaaS startup in an interesting process during which I learned a ton.  So we’ve got a lot of experience to draw upon.

SaaS startup CEO is hard job.  It’s a lonely job, something people don’t typically understand until they do it.  It’s an odd job — for what might be the first time in your career you have no boss, per se, just a committee.  You’re responsible for the life and death of the company.  Scores or hundreds of people depend on you to make payroll.  You need to raise capital, likely in the tens of millions of dollars — but these days increasingly in the hundreds — to build your business.

You’re driving your company into an uncertain future and, if you’re good, you’re trying to define that future your way in the mind of the market.  You’re trying to build an executive team that not only will get the job done today, but that can also scale with you for the next few years.  You’re trying to systematize the realization of a vision, breaking it down into the right parts in the right order to ensure market victory.  And, while you’re trying to do all that, you need to keep a board happy that may have interests divergent from your own and those of the company.  Finally, it’s an accelerating treadmill of a job – the better you do, the more is expected of you.

Wait!  Why do we do this again?  Because it’s also a fantastic job.  You get to:

  • Define and realize a vision for a market space.
  • Evangelize new and better ways of doing things.
  • Compete to win key customers, channels, and partners.
  • Work alongside incredibly talented and accomplished people.
  • Serve the most leading and progressive customers in the market.
  • Manage a growing organization, building ideally not just a company but a culture that reflects your core values.
  • Leverage that growth internationally, exploring and learning about the planet and the business cultures across it.

Basically, you get to play strategic N-dimensional wizard chess against some of the finest minds in the business.  Let’s face it.  It’s cool.  Despite the weight that comes with the job, any SaaS startup CEO should feel privileged every day about the job that they “get to” do.

But there are certain nagging questions that hound any SaaS startup CEO.  Questions that never quite get answered and put to bed.  Ones that need to asked and re-asked.  Those are the 5 questions we’ll discuss in my talk.  And here they are:

  1. When do I next raise money?
  2. Do I have the right team?
  3. How can I better manage the board?
  4. To what extent should I worry about competitors?
  5. Are we focused enough?

Each one is a question that can cost you the company, the market, or your job.  They’re all hard.  In my estimation, number 4 is the trickiest and most subtle.  There’s even a bonus question 6 – “are we winning?” — that is perhaps the most important of them all.

I look forward to speaking with you and hope you can attend the session.  If you have any advance questions to stimulate my thinking while preparing for the session, please do send them along via email, DM, or comment.

You don’t need to be a CEO to benefit from this session.  There are lots of lessons for everyone involving in creating and running a startup.  (If nothing else, you might get some insight to how your CEO might think about you and your team.)

I hope to see you there.

Are You a “Challenging” or Simply a “Difficult” Direct Report?

Most managers, save for true sycophants, want to challenge their boss.  Few managers want to be puppet yes-people to the boss.  They’ve worked hard to get where they are.  They bring years of wisdom and experience.  They want to push and challenge.  But many don’t know when or how.  More importantly, they don’t know what they don’t know.

How often do you think you’re challenging the boss when he/she thinks you’re just being plain difficult?  Challenging direct reports keep their positions and rise with the organization.  Difficult ones get jettisoned along the way.

There are two great ways you can figure out how often you’re being which:

  • Think of things from the boss’s perspective
  • Ask the boss

Think from the Boss’s Perspective

Bosses want to get things done.  Things generally fall into two buckets:  easy and hard.  Easy things may still entail a lot of work and planning, but there’s nothing really conceptually difficult or unknown about them.

Running the company’s presence at a tradeshow you attend every year might be a lot of work, but I’ll consider it easy for this conversation because that work is known.

Deciding to terminate a problem employee is easy.  (Note inclusion of word “problem.”)  If you see a problem, the adage goes, everyone else has probably already seen it for months and the damage done is more than you know.  This decision is hard from a personal perspective — I’ve never met anyone who enjoys terminating people.  But firing someone who routinely misses deadlines, training sessions, and team meetings isn’t hard in this context.

Launching the new version of a product is easy.  Yes, the positioning may be hard, but managing the overall launch process is easy.   It’s hopefully done a few times per year.  Yes, it’s a lot of work and planning, but there’s nothing conceptually difficult about running the process.

Difficult direct reports make easy things hard.  How?

  • Complexification.  When you ask someone the time you discover that there are three types of people in the world:  those who tell you the time, those who tell you how to build a watch, and those who tell you how to build a Swiss village.  Simplifiers go far in organizations, complexifiers get stuck.
  • Lack of follow through.  Bosses want to talk once about a project, agree to it, and then have it get executed.  As my friend Lance Walter always said bosses want “set it and forget it” direct reports.  If you have a question, come ask.  But otherwise I assume you are tracking our agreed-to objectives and they’re going to happen without me having to check and re-check.  Ditto for feedback given along the way.
  • Drama.  Difficult directs tend to take things personally.  They turn criticism of work into criticism of them.  They view a heavy workload as dramatic sacrifice and not a prioritization problem.  They are sensitive to criticism, defensive when questioned or given feedback, and often unable to separate bad performance from bad intent.

The result is that over time the boss starts to loathe the idea of meeting with the direct report which results in a downward spiral of communication and relationship.

Challenging direct reports keep easy things easy.  They get shit done without a lot of supervision, complexification, or drama.  On the flip side, challengers don’t just go along for the ride when it comes to inherently hard things like fixing a break in the sales pipeline, selecting company or product strategies, or working on a competitive campaign strategy.  They weigh in, sometimes challenging the majority or consensus view.  They provide good arguments for why what everyone else is thinking could be wrong.  Their selective Devil’s advocacy helps the company avoid groupthink and the organization make better decisions.  And they do this without going overboard and positioning themselves as the resident contrarian.

Simply put, when you say something to the boss or in a meeting, imagine how the boss will react and then count the ratio between the following two reactions

  • God, what a pain in the ass.
  • Wow, I hadn’t thought of that.

Ratios above 1.0 indicate you are a net difficult direct report.  Ratios below 1.0 indicate you are a net challenger.

Ask the Boss

Since knowing is always superior to guessing, I’ll give you a set of good questions that can help you figure out where you stand.

  1. If you had to rank your direct reports from top to bottom in terms of difficultly, would I fall above or below the median and why?
  2. Can you please list 3-5 things I do that make it difficult to manage me so I can work on them?
  3. To what extent do you find me difficult/contrarian for difficulty’s sake vs. genuinely challenging ideas and helping the company reach better decisions?
  4. When it comes to strategic debates do you feel that I sit on the sidelines too much, participate too much, or strike a good balance?
  5. If there is a pattern of skipped/cancelled 1-1’s (a sign of avoidance) or higher frequency 1-1’s with other directs, then ask why?

Sycophants know they are sycophants.  Challengers usually know they are challengers.  The risk is that you are a difficult when you think you’re a challenger — and that rarely ends well.  So think about, ask, and take appropriate measures to correct the situation.  Before your boss doesn’t want to talk to you anymore.