Jun 1 2023

The Ladder of Inference

Last week, I wrote about Inquiry vs. Advocacy, an important principle I learned early in life and then explored more deeply in an Action/Design workshop my coach Marc took our whole leadership team through years ago.

This week, I’ll continue to riff on the theme of communications tools in the CEO toolbelt by talking about The Ladder of Inference (detailed article here). This is a great graphic from the article:

Any time you’re struggling with opinions vs. opinions or people are jumping to conclusions based on a narrow set of evidence, this framework is your friend. The best way to start any tricky conversation with those characteristics is to start “at the bottom of the ladder,” meaning you start by reviewing the available data on the topic at hand. As John Adams said, “facts are stubborn things,” so start by agreeing on a common set of irrefutable data on the topic. Then you can take a step up the ladder to a more productive conversation about interpretations, then ultimately come to decisions or conclusions.

Jim Barksdale, the former CEO of Netscape had a great saying that supports this principle, too: “If we have data, let’s look at the data. If all we have are opinions, let’s go with mine.”

The language our team developed around this is easy. It’s like a safe word. Any time someone is jumping to conclusions without being rigorous about the underlying data, they’ll be the recipient of a comment like “wow you went right up to the top of the ladder on that one!” Either that, or someone will pull out a wonderful reference to Office Space.

Comments
May 25 2023

Book Short: Boards That Lead

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.

Comments
May 18 2023

What Does Great look Like in a Chief Privacy Officer?

(This is the second post in the series… the first one When to Hire your first Chief Privacy Officer is here)

Most Chief Privacy Officers are fairly specialized, often coming from a legal or law enforcement background, but regardless of background I’ve found that ideal startup Chief Privacy Officers do three things particularly well.

First, a great Chief Privacy Officer will work to create educated evangelists inside the company.  Our Privacy team at Return Path, under Dennis Dayman’s leadership, had a lot of experience and industry certifications, but that experience was not something only for regulators and other companies, or only bragging rights within their team. They also took the time to make sure others in the company, especially in the product management and engineering teams, received some of that same training and those same certifications.  By not making the Privacy team a single point of knowledge or failure, Dennis was able to make Privacy part of our product strategy and offense as opposed to a mitigation or defensive function

A second ideal characteristic of a Privacy Officer is that they also handle the basics of InfoSec, in addition to privacy.  If you’re actually a security-related company or a massive consumer or financial organization, you may need a dedicated Chief Information Security Officer.  If you aren’t, then a good Chief Privacy Officer should be able to handle a number of the functions that a CISO would otherwise handle, especially on the policy and communication front.

And third, a great Chief Privacy Officer is an excellent communicator, both internally and externally, and they help connect you to the relevant members of your community or ecosystem.  When we had a sizable data breach on Thanksgiving Day about 10 years ago, our fractional head of privacy, Tom Bartel, was on the spot. He wrote emails and external blog posts that needed almost no review.  He was also instantly communicating with dozens of his counterparts at related companies so that the industry knew where we stood and what we were doing about the problem.  It was like an instant activation of an emergency response system!

Don’t wait until you have a data breach to hire a great Chief Privacy Officer because by the time you need one it will be too late.

(You can find this post on the Bolster Blog here)

Comments
May 11 2023

Inquiry vs. Advocacy

My Grandpa Bill used to not want to talk about himself at dinner parties. When one of us asked him why one day, he said, “I already know what I have to say. What I don’t know, is what the other person has to say.”

There are a few principles I learned years ago in a workshop that my coach Marc led for us called Action/Design. I’m going to try writing a few posts about them, and you can find some articles on them here.

Inquiry vs. Advocacy is simple. Understand the balance of when you ask and listen vs. when you speak in a given conversation. Both are important tools in the CEO tool belt.

My rule of thumb is to ask and listen more than you speak. It’s the only way you will learn, collect data on your organization and on your customers and products. Early in your career, you should primarily be Inquiring. Even mid- and later career people who sometimes must be in a position to speak or advocate their point of view benefit most when they ask and listen and learn.

More important, though, Inquiry vs. Advocacy is the best way to guide your communications in a difficult conversation, complex negotiation, or tricky situation. And it’s in those kinds of situations that you actually need to be cognizant that both approaches are important, and you need to know which one to pull out when and pay attention to how others in the conversation are using the two as well. From an article in the resource center I linked to above:

In conversations on complex and controversial issues, when there is a high degree of advocacy and little inquiry, people are unable to learn about the nature of their differences. People may feel the speaker is imposing a view on them without taking into account their perspective, which can lead to either escalating conflict or withdrawal. When there is a high degree of inquiry, but no one is willing to advocate a position, it is difficult for participants to know where the other stands, and the lack of progress can lead people to feel frustrated and impatient. As a participant in a conversation, being aware of the balance of advocacy and inquiry can help you determine how best to contribute at a given time. If you hear that people are advocating but not asking questions, inquire into their views before adding your own. If you hear people asking questions for information but not stating an opinion, advocating your view may help the group move forward.

Inquiry vs. Advocacy has become a cornerstone of how I think about communicating and learning. I like to think I learned it from Grandpa Bill first, but the Action/Design work with my coach, and then years of practice, drove it home.

Comments
May 4 2023

When to Hire a Chief Privacy Officer

(Post 1 of 4 in the series of Scaling CPO’s)

 Most startups don’t have a Chief Privacy Officer and just rely on outside advice from external counsel or a privacy consultant. In Startup CXO our Chief Privacy Officer from Return Path, Dennis Dayman, strongly advocates for privacy to be baked into a startup at the very beginning. Some startups probably don’t have any help in this area at all but given the importance of privacy and security issues today that’s a mistake.

If your startup doesn’t start life with a Chief Privacy Officer you’ll have to heed some warning signs and here are some I’ve picked up over the years. First, you’ll know it’s time to hire a Chief Privacy Officer when you wake up in the middle of the night terrified that you’re going to find your company on the front page of the newspaper or served a subpoena to testify before Congress about a data breach. Even if you’re not waking up in the middle of the night you might be concerned about privacy if you are spending too much of your own time trying to understand what PCI Compliance, or HIPAA, or GDPR means to your business. Or if you really don’t see the connections between your business and privacy issues in general, then a Chief Privacy Officer can be very helpful.

You might get tough questions from your board on what your data breach client communication plan is, and if you don’t have a great answer and aren’t sure how to get to one, then it’s time to think about a Privacy Officer.

A fractional Chief Privacy Officer may be the best option for most startups…forever. Sometimes you can find one fractional executive for both the Privacy and Chief Information Security Officer roles. You probably can’t get by without a full-time leader in this area if you are large (>$50mm in revenue) and are sitting on a massive amount of consumer data, especially if that information involves PII, financial, or health information.  But if that’s not you, a fractional Chief Privacy Officer may be the way to go.  While a fractional executive is similar to an outside lawyer or consultant, an executive has a company title for external credibility and the personal commitment to the organization to ensure compliance. A fractional exeuctive is way more than a consultant since they’ll be able to provide guidance to employees and represent the company as if they were a full-time Chief Privacy Officer.

Not every startup needs a Chief Privacy Officer since you can cover your bases with lawyers or consultants, but if you’re collecting lots of data from jurisdictions across the world you’d be wise to get a Privacy officer, or a fractional executive, sooner rather than later.

(You can find this post on the Bolster Blog here)

Comments
Apr 27 2023

Bring People Along for The Ride, Part II of II

Last week, I wrote about Bringing People Along for The Ride by involving people in the process of ideating and creating change in your organization. That’s the most important thing you can do to make it easy for people to handle change.

But what about the people you don’t or can’t bring along for the ride in that way? If you organization has more than 10 people in it, there will inevitably be people where you’re IMPOSING CHANGE ON THEM. And honestly, even people who are involved in designing change still have to live through its impact.

Today’s post is about managing the actual impact.

The best thing you can do as a leader in helping your organization navigate change is to be empathetic to the fact that, even if you involve people in designing the solution, you are, in fact, making changes to their day to day lives. One of the best books I’ve ever read on this is Transitions: Making Sense of Life’s Changes, by William Bridges. And while there’s a lot more to the book than this one point, I’ll share two graphics from the book and its offshoots that say a lot.

Bridges’ basic concept is to think about changes as having three phases. The end of the old thing, the beginning of the new thing, and the time between the two – when the new thing has been announced, but the it hasn’t taken effect yet. Here’s a look at one powerful graphic on this front, where the point is that productivity (the red line) tanks briefly during the time of uncertainty with the overlay of human emotions at each phase.

Next let’s look at Bridges’ model for how to think about these three phases. This part is critical. They are not discrete phases, where everyone finished “ending” and moves onto “neutral” and then moves on to “new.” From the moment a change is in the offing, until after the change is implemented, people are simultaneously operating in all three zones at the same time, in different proportions.

That means when change starts, you’re already helping them understand that there will be a period of confusion followed by a bright new future. And it means that even when the bright new future has arrived, you’re still mindful of the confusion as well as the things that were special about the past.

I wrote about this a little bit in the second edition of Startup CEO and in this blog post on transitions and integration. The paragraph I’ll call out is:

For ourselves as leaders and me as CEO, knowing most of us would leave almost immediately post-deal, I wanted to have as elegant an exit as possible after 20 years. Fortunately, I had a good partner in this dialog in Mark Briggs, the acquiring CEO. Mark and I worked out rules of engagement and expenses associated with “the baton pass,” as we called it, that let our execs have the opportunity to say a proper goodbye and thank you to our teams, with a series of in-person events and a final RP gift pack. This was a really important way we all got closure on this chapter in our lives

The Baton Pass is a helpful analogy to think about this process. In a relay race, the two runners run alongside each other for a little while until they are at the same pace and proper spot, THEN one hands the other the baton. It’s the time when the past and the future collide, in a neutral zone. When you mark the great things and painful learnings that came before and launch into the bright new future.

The best thing you can do as a leader who is driving change through an organization is to Bring People Along for the Ride. Part of that is involving people in the creation of the new world. But it’s also recognizing that humans have to process change, and that takes time.

Comments
Apr 20 2023

Bring People Along for The Ride, Part I of II

One of the CEOs I mentor asked me the other day asked me this question:

I need to start making my organization think differently – more like a startup that needs to scale and less like a project. People need to start doing more specific jobs and not swarm all over everything. How do I get people to “get” this without freaking out?

Every CEO faces dilemmas like this all the time.

One of my management mantras over the years has been, “You have to bring people along for the ride.” Fundamentally, that means two things. I’ll write about one of them here today and save the other for next week.

First, bringing people along for the ride means you have to involve the people in the organization in the origins and design of the change you’re seeking to drive.

Let’s face it. No one really likes change. But what people really don’t like is change being IMPOSED ON THEM, especially where THEY DON’T UNDERSTAND WHY.

Without being disingenuous, you as a leader can set the stage for others in your organization helping you with changes — even if you generally know the changes you want to drive. Bring people together. Talk about the challenges you see that are related to the solution you’re contemplating. Get people talking, brainstorming, grabbing post-its and whiteboard pens. Talk a little bit – bring in your perspective and help shape the discussion. But also listen closely and be open to people’s ideas and let those shape the outcome as well.

Then, bring people back for a second and third meeting to then react to some of your idea distillation and even straw man plans. You’ll find that process not only produces a better solution but also makes people comfortable with the solution, because you’ve added more transparency to the equation and brought people along for the ride. Nothing done in the vacuum of the CEO’s mind achieves this same level of impact.

More thoughts on this to come in some related posts over the next couple of weeks around some geeky sounding terms like The Ladder of Inference, Inquiry vs. Advocacy, and Double Loop Learning. Next week’s post will be about how to think about transitions and the way to lead people through them once you’ve involved them in creating the transition. Its link won’t be live until April 20, but it’s here for future reference.

Comments
Apr 12 2023

Daily Bolster Weeks 1 and 2 recap

We have a little more than two weeks of The Daily Bolster podcast under our belts now, and we’re off to a great start! I announced it here, and I thought I’d post links to the first bunch of episodes…I don’t think I’ll do this regularly, though. You can listen to all episodes here (or on your favorite podcast platform), and never miss an episode when you sign up for daily email notifications.

Episode 1: 3 Tips to Scale Your Culture with Nick Mehta

Our very first guest on The Daily Bolster was Nick Mehta, CEO of Gainsight. As an early-stage startup or a small business, you have significant influence over the culture—but what happens when you’re one of many? Nick and I discussed what happens to company culture when you achieve your scaling and growth goals.

Episode 2: Managing Up with Cristina Miller

Executives are often caught in the middle of the leadership dynamic, managing both up and down the organization. Cristina Miller—a seasoned, results-driven executive and board member (including on Bolster’s board!) with a strong track record—shared what it looks like to set expectations and build a strong relationship with your CEO.

Episode 3: Common Mistakes Founders Make with Fred Wilson

Fred Wilson has been a venture capitalist since 1987 and has worked with me for over 20 years now—so it’s fair to say he’s witnessed a few founders and become familiar with their most common mistakes. Listen to this episode to learn how to recognize and avoid those mistakes for yourself.

Episode 4: Cultivating Talent to Promote Internally with Nick Francis

In this episode, Nick Francis—co-founder and CEO of Help Scout—joins me to discuss what it takes to cultivate in-house talent and embody organizational values. I talk about my playbook for building effective teams and developing leaders with a growth mentality as part of this.

Episode 5: Deep Dive with Jeff Epstein

Career shifts are more common now than ever, even for senior executives. Experienced CFO and operator (and one of my former board members) Jeff Epstein joined me for an extended episode about the ins and outs of career transitions and the surprises that come with them, from role changes to new industries to vastly different organizational structures. Tune in to follow the shifts in Jeff’s career journey, hear about the lessons he learned firsthand, and get his advice for founders looking to scale. “I always wanted to develop a circle of competence and then over time expand the circle,” Jeff says. “You just learn more.”

Episode 6: Hallmarks of Successful Founders with David Cohen

David Cohen, Founder and Chairman at Techstars, shares the top three signs he looks for that differentiate successful founders—things that are nearly impossible to fake. Either you have them, or you don’t. This one is awesome.

Episode 7: Success as a Fractional Exec with Courtney Graeber

If you know anything about Bolster, you know we’re a champion for fractional executives. As an Interim Chief People Officer, HR Executive Consultant, and trusted mentor to executive teams, Courtney Graeber provides feedback and recommendations that enhance organizational culture and attract, develop, and retain top talent. Many of her clients are navigating transitional periods—and that’s where Courtney’s expertise comes in. Listen in to learn what it’s like to be (or work with) a fractional head of people.

Episode 8: 3 Ways VCs Say “No” Without Saying “No” with Jenny Fielding

It’s important for founders to be able to hear what’s left unsaid in conversations with VCs. Sometimes, says one of NYC’s top pre-seed investors Jenny Fielding, VCs aren’t ready to invest in a startup, but they’re not ready to say no, either.  Here, Jenny shares three signs a VC may be saying “no” without saying the words—and what founders should do next.

Episode 9: Building a Strong Culture with Jailany Thiaw

Jailany Thiaw, founder and CEO of UPskill, a future-of-work startup automating feedback in entry-level hiring pipelines, joins me to discuss the best ways to get company buy-in as you build and maintain a strong and welcoming culture—especially in an early stage or remote environment.

Episode 10: Deep Dive with Brad Feld

Brad Feld is partner and co-founder of Foundry, and a long time early stage investor and entrepreneur who I’ve also worked with for more than two decades. In this episode, he and I take a deep dive into how startups and venture capital have changed over the past 25 years—and what has stayed the same.  They also discuss the dynamics of startup boards, along with common characteristics that make founders or companies successful at scale.

Episode 11: The Value of Podcasting with Lindsay Tjepkema

This episode is all about podcasting. Meta, right? Lindsay Tjepkema is the CEO and co-founder of Casted, the podcasting solution for B2B marketers.  She and I dive into the reasons why podcasts are such a great way to get your voice—literally—out into the world. Tune in to hear Lindsay’s tips for starting a podcast as a CEO, setting expectations, asking meaningful questions, and creating human connection. We’ve loved partnering with Lindsay and her team so far on The Daily Bolster!

Episode 12: Interviewing for “Culture Fit” with Rory Verrett

What does it mean to interview for culture fit? How should CEOs and leaders go about doing it—and is there a better way? Rory Verrett is the founder and managing partner of Protégé Search, the leading retained search and leadership advisory firm focused on diverse talent, and is also on Bolster’s Board of Directors. He and I discuss why CEOs are not always the best arbiters of company culture, then we dive into what it means to look for specific values throughout the interview process, rather than the vague concept of a culture fit.

The Daily Bolster is for people in the startup world want to hear from industry experts of all backgrounds, but don’t always have the time to listen to full length interviews, even at 2x speed. Instead, we’re getting straight to the point with mostly 5-minute episodes. Any and all feedback welcome!

Comments
Apr 6 2023

Collecting Feedback from Your Board

A friend of mine just emailed me and asked how I collect feedback from the Board after Board meetings. I have a good routine for this which I wrote about a little bit here but have since expanded.

First, we are disciplined about leaving an hour at the end of the board meeting for the following three things :

  • Executive session – directors only, including me – sometimes I’ll have my CFO Jack come for a few minutes at the beginning, depending on the topics. The topics can be about people on the team, or things I’m concerned about that I didn’t want to talk about with observers and team present. I tee up any topics in a separate memo that I send only to board members when I send the main board book out. My board meetings are very inclusive – lots of team members and observers present, so it’s good to have this time available case the Board wants to talk more openly with me about something or ask questions they didn’t feel like asking with the broader group in the room.
  • Closed session – I leave, so I give non-management directors an opportunity to talk about any issues related to me.
  • CEO Debrief – I ask one director to take notes for me during Closed Session, then that person calls me back in to debrief anything.

All three of these are important, and it’s important to do them every meeting, even if you don’t have any specific issues to discuss. That way, no one freaks out (including you) if suddenly and unexpectedly, there’s a part of the meeting to which they’re not invited.

The key to this is really leaving time for it. Now that board meetings are often on Zoom, a lot of CEOs have shrunk the time to 2-3 hours to avoid Zoom fatigue, but that doesn’t usually leave a full hour for this end-of-meeting routine. Finish your main meeting, give everyone 10 minutes to breathe, then come back for the final three steps of the meeting.

Then, I use this form after every meeting, which was a suggestion from Fred a few years back (not here or here, though these are also really good posts he wrote on this topic). I sent it during Executive Session and ask people to fill it out immediately after the meeting while things are fresh in their minds.

Quick, easy, effective. You should never finish a Board meeting and have no idea how it went.

Comments
Mar 30 2023

Grow or Die

My cofounder Cathy wrote a great post on the Bolster blog back in January called Procrastinating Executive Development, in which she talks about the fact that even executives who appreciate the value of professional development usually don’t get to it because they’re too busy or don’t realize how important it is. I see this every day with CEOs and founders. Cathy had a well phrased but somewhat gentle ask at the end of her post:

My ask for all CEOs is this: give each of your executives the gift of feedback now, and hold each other accountable for continued growth and development to match the growth and development of your company.

Let me put it in starker terms:

Grow or Die.

Every executive, every professional, can scale further than they think is possible, and further than you think is possible. Most of us do have some ceiling somewhere…but it will take us years to find it (if we ever find it). The key to scaling is a growth mentality. You have to not just value development, you have to crave it, view it as essential, and prioritize it.

Startups are incredibly dynamic. You’re creating something out of nothing. Disrupting an industry. Revolutionizing something. Putting a dent in the universe. For a startup to succeed, it has to constantly put something in market, learn, calibrate, accelerate, maybe pivot, and most of all grow. How can a leader of a startup scale from one stage of life to the next without focusing on personal growth and development if the job changes from one quarter to the next?

I was lucky enough to have a great leadership team at my prior company, Return Path, over the course of 20 years. Within that long block of time with many executives, there was a particular period of time, roughly 2004-2012, that I jokingly refer to as the “golden age.” That’s when we grew the business from roughly $5mm in revenue to $50 or $60mm. The remarkable thing was that we executed that growth with the same group of 5-6 senior executives. A couple new people joined the team, and we struggled to get one executive role right, but by and large one core group took us from small to mid-sized. Why? We looked at each other — literally, in one meeting where we were talking about professional development — and said, “we have to commit to individual coaching, to team coaching, and to growth as leaders, or the company will outpace us and we’ll be roadkill.”

That set us on a path to focus on our own growth and development as leaders. We were constantly reading and sharing relevant articles, blog posts, and books. We engaged in a lot of coaching and development instruments like MBTI, TKI, and DISC. We learned the value of retrospectives, transparent 360s, and a steady diet of feedback. We challenged ourselves to do better. We worked at it. As one of the members of the Golden Age said of our work, “we went to the gym.”

The “Grow or Die” mantra is real. You can’t possibly be successful in today’s world if you’re not learning, if you don’t have a growth mentality. You are never the smartest person in the room. The minute you are convinced that you are…you’re screwed.

If you don’t believe me, look at the development of your business itself as a metaphor for your own development as a leader. What happens to your startup if it stops growing?

(You can find this post on the Bolster Blog here)

Comments
Mar 23 2023

Announcing The Daily Bolster (You DO NOT want to miss this new Podcast)

I’m thrilled to announce The Daily Bolster — a quick-hitting podcast for startup leaders scaling their businesses. It’s the actionable insight you need to scale—in about 5 minutes. The first episode drops this coming Monday.

Our team created The Daily Bolster for folks in the startup world who — like me — want to hear from industry experts of all backgrounds, but don’t always have the time to listen to full length interviews, even at 2x speed (which usually ends up sounding like Alvin & The Chipmunks, anyway).

Instead, we’re getting straight to the point. GTTFP, as Brad says.

Starting next week, I will be joined every day by experienced operators and industry experts who share their real-world experiences and practical advice. Each day of the week, we’ll cover a different topic or theme:

  • Monday: CEO Tips & Tricks
  • Tuesday: Scaling Yourself & Your Team
  • Wednesday: The View from the Board Room
  • Thursday: Ask Bolster (this one will be more like 20-30 minutes to go deeper with someone)

The schedule is jam-packed with dynamic guests and punchy interviews. Whether you tune in every day, when you see a guest you’re especially interested in, or only on Tuesdays, we’re so excited to share these conversations with you.

In Week 1, I welcome Gainsight CEO Nick Mehta, board member extraordinaire and marketplace guru Cristina Miller, Union Square Ventures partner Fred Wilson, Helpscout CEO Nick Francis, and Bessemer Operating Partner and veteran CFO Jeff Epstein. They’ll share their practical advice and real-world experiences around professional development, company culture, startup strategy, and tips and tricks for executive growth.

Check out the season preview to learn more. You can also sign up for email notifications, to make sure you never miss an episode. The daily email will also include a pull quote and clips in case even the 5-minute version is too long for you.

You can subscribe to The Daily Bolster on these platforms: Bolster, YouTube, Apple, Google, Spotify, Amazon, Stitcher, Pandora, and Castbox, plus we’ll put each episode up on LinkedIn and Twitter. You should either follow me (T, LI) or Bolster (T, LI) on those to see the content.

Comments