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Jul 11 2004

Turning Lemons into Lemonade

I’ve always thought that the ability to stare down adversity in business — or turning lemons into lemonade, as a former boss of mine used to say — is a critical part of being a mature professional. We had a prime example of this a couple weeks ago at Return Path.

We had scheduled a webinar on email deliverability, a critical topic for our market, and the moment of the webinar had come, with over 100 clients and prospects on the line for the audio and web conference. There was a major technical glitch with our provider, Webex (no link for you, Webex), and after 5 or 10 minutes, we had to cancel the webinar — telling all 100 members of our target audience that we were sorry, we’d have to reschedule. What a nightmare! Even worse, Webex displayed atrocious customer service to us, not apologizing for the problem, blaming it on us (as if somehow it was our fault that half the people on the line couldn’t hear anything), and not offering us any compensation for the situation.

As you can imagine, our marketing guru Jennifer Wilson was devastated. But instead of sulking, she turned the situation on its head. She rescheduled the event for three weeks out with a different provider who was technically competent and a pleasure to work with, Raindance, and sent every person who’d been on our aborted webinar a gift certificate to Starbucks so they could enjoy a snack on our dime during the rescheduled event. Not only did we have full attendance at the rescheduled event, but Jennifer received dozens of emails from clients sympathizing with her, commending her on her attitude, and of course thanking her for the free latte.

It’s hard to do, and you hate to have to do it, but successfully turning lemons into lemonade is one of the most satisfying feelings in business!

People rarely comment on this blog (or most non-political blogs, I’ve noticed), so feel free to share your best lemons-to-lemonade story with me in a comment, and I promise I’ll post the best couple of them pronto!

Feb 9 2023

Swoop in, Swoop out

A fellow CEO with whom I’m friendly was venting to me the other day about one of their Board members. They were stunned that the lived experience they have day in, day out running the business wasn’t something the director internalized at all — and this is a good, well known, high quality VC director.

I pointed out that VCs are on lots of boards and can’t get in the headspace of all their CEOs all the time, although the good ones don’t just swoop in and swoop out but do take the time to track all the significant things and the nuances with all their portfolio companies.

My friend, the CEO, had a brilliant comeback line that is worth sharing and documenting here. Their company is going through a tough time at the moment like so many companies. Layoffs, missed numbers, uncertain future. The line was:

It’s my shit show, he just makes a cameo appearance in it once in a while

That pretty much sums up the difference between the operator and the director!

Aug 25 2004

Wrap-up on Preferences?

In this Olympic Season, Brad gets the gold medal and possibly world record for longest post with his excellent posting on Participating Preferred securities. Fred gets the silver with his contribution on The Double Dip. Dave Jilk and others share the bronze for their many comments.

I won’t add more to the debate but will try to close it by tying together a few of these postings. Fred and Brad both wrote subsequent postings on the related themes of If It Looks Too Good to Be True, It Probably Is and Fantasy vs. Reality. These comments could easily be applied to my thoughts on VCs being silly about bidding up crazy long shot concepts and committing Venture Fratricide.

And of course, it begs the new media version of the age-old question: if a web service costs $25 million to build and then falls into the ether while investors and management sheepishly turn their backs, does it make any noise?

May 20 2010

Call Me

Call Me

A fine song by Blondie from 1980 and from the soundtrack of the movie American Gigolo.  And also something that reminded me about the importance of not relying too much on email this past month. 

 I had surgery on my left wrist in early March to hopefully fix a nagging tendonitis problem.  And while I could still write and type post-op, I got sore pretty quickly every day, so I tried to keep those activities to a minimum.  As you might imaging, I do an awful lot of email and IM in my line of work.  So what was my short response to a huge number of emails and IMs for a few weeks?  “Call me.”

 My communications, especially with remote employees, not only didn’t suffer while I couldn’t type a lot – they were stronger than ever.  Even short, two-minute phone conversations – the remote equivalent of someone sticking their head in my office – are preferable to IM or email in many cases.  There’s nothing like the sound of someone’s voice to add real texture to a dialog and to avoid misunderstandings.

Aug 12 2005

Email and Business Development: Two Great Tastes…

Email and Business Development: Two Great Tastes…

Interestingly, Chris Baggott offers compelling evidence for the opposite view he intended in his recent posting claiming email is not an acquisition tool.  I respect Chris as a thought leader in the email marketing services industry and am a fan of what he and his colleagues have done in building Exact Target, but I think he’s dead wrong on this one.

Email is a phenomenal customer retention tool, no question about it.  I totally agree with the claim that website owners should never let a prospect escape from their website without signing up for an email program.  It’s very true that spending money on website traffic can go to waste if a browser never buys or returns — or worse, if you pay the same search keyword fee time and time again to reach the same browser. 

However, his own post starts to lay out the reasons why email is, in fact, also really good for acquisition marketing:  because we all still love it, we spend a lot of time reading and responding to it, and we value the information it brings to us.  In short , it’s got all the strongest attributes of a great acquisition medium: reach, frequency and, most importantly, trust.  Isn’t that what advertisers look for when they are trying to figure out whether to spend their acquisition dollars in print, radio, TV, outdoor, or direct response vehicles?

In fact, more consumers and B2B professionals spend more time in their inboxes than they do consuming any other form of media — digital or not.  So, if you want to reach your target, you need to be using acquisition email.  And definitely never let a prospect come to your web site without giving you his or her email address for future contact!

Just because email is so extraordinary a retention and customer relationship tool, doesn’t exclude the reality that it also works really well to reach new prospects.  Smart marketers use email for both.

May 14 2015

Give the Gift of a 360 to Your Board of Directors

Give the Gift of a 360 to Your Board of Directors

I recently ran our biennial Board 360, and I thought it would be interesting to share the details.  Attached are a few pages from, my book, Startup CEO:  A Field Guide to Scaling Up Your Business  which describe the process as well as share the survey I developed, which I adapted from one that the legendary Bill Campbell uses at larger public companies like Intuit.

If you’ve read this blog a lot over the years, you know that we are big on 360s for staff at all levels at Return Path , and at some point a few years ago, I thought, “hmmm, shouldn’t we do this for the Board as well?”

Most of our directors had never been part of one before as Board members, and they reacted to it with varying levels of interest and trepidation.  But all of them loved the output and the discussion we had afterwards.  Extending the level of transparency we have internally to the Board was a great thing and a great use of time, and I think making the Board members review themselves and their peers critically and then seeing the results sharpened overall Board performance.

The document also shares the survey we use, which we have each director take anonymously and compile the results to share in Executive Session at a Board meeting.  We also ask a few members of the senior management team to fill out the survey as well so the Board gets feedback from them, too.

May 16 2006

Sticking it to United, Just a Little Bit

Sticking it to United, Just a Little Bit

I am sitting in the Red Carpet Club waiting for yet another delayed United flight, and there’s a small thing bringing me a little extra joy. I recently started using Verizon’s Broadband Wireless service, which is expensive at $60/month, but awesome since it basically works anywhere and eliminates the need for hotel, Starbucks, and other Wi Fi hot spot fees (and for a great tutorial on how to use the service to power two computers at once, read Brad’s post here).

I’ve long been annoyed at United — and American as well — for both charging a pretty sizeable annual fee to belong to their airport clubs and then soaking me for another $10 every time I’m in one just to use their T-Mobile hot spot.  Many people, including Fred here, believe that Wi Fi should be free everywhere.  While I think that’s a great idea, I don’t think it’s a god-given right.  And I don’t mind that Starbucks charges me to use their hot spots, since I may only be spending a couple dollars with them.  However, airline clubs that charge a lot of money for membership should definitely include WI Fi as part of the deal.

So my great joy today was *not* giving yet another $10 to United for the privilege of using the Internet. Thank you, Verizon (not that I don’t also have various complaints about Verizon, but that’s for another day).

It truly is the little things…

Aug 27 2015

The Joy of Coaching

I was the head coach of my two older kids’ little league team this past spring.  The whole thing was a little bit of an accident – I vaguely volunteered for something and ended up in charge.  The commitment was a little daunting, but I was ok with it since the season was only a couple months long, it was both Casey and Wilson, and both kids, especially Wilson, are really into baseball.  Other than helping out a bit here and there, I’d never coached a sports team before.

What started off as an unclear assignment ended up as one of the most fun and fulfilling things I’ve done in years.  I loved every minute of it, looked forward to our practices and games, was hugely bummed out when we got rained out, and never had a moment where I couldn’t make the time for it (though clearly the hours had to come from somewhere!).  Given some of the overlap between leading a sports team and leading a company, I thought I’d reflect on the experience a bit here.  There are some common themes between this post and something I wrote years ago, Parenting and Corporate Leadership, with the same caveat that no, I don’t think employees are children or children are employees.  But here are some things I take away from the experience and apply or compare to work.

We established a clear philosophy and stuck to it.  That’s a step that lots of coaches – and managers in the workplace – miss.  The other coaches and I discussed this before the first practice, agreed on it, and shared it directly with the kids.  For this age group in particular, we felt that we were there first and foremost to have fun; second to learn the game; and third, to play hard and fair.  Note there was nothing in this about winning, and that we were really specific about the order of the three objectives.  Even 7 and 8 year olds know the difference between “win at all costs” and “have fun and play ball.”  We reinforced this at every practice and at every game.  Being intentional about a philosophy and communicating it (and of course sticking to it) are key for any leadership situation.

We got lucky.  As I repeatedly said to the parents on the team, we had a group of awesome kids – happy and generally paying attention, and not one troublemaker in the bunch; and we had a group of awesome parents – responsive, supportive, and not a single complaint about what position a kid was playing or where someone was in the batting order.  I’d heard horror stories about both kids and parents from other coaches ahead of time.  It’s possible that the other coaches and I did such a good job that both kids and parents were great all the time…but I think you have to chalk most of that up to the luck of the draw.  Work isn’t all that different.  Having stakeholders who are consistently positive forces is something that sometimes you can shape (you can fire problematic employees) but often you can’t, in the case of customers or even Board members.  Luck matters.

Stakeholder alignment was a critical success factor.  Having said that, I do think the coaches and I did a good job of keeping our stakeholders aligned and focusing on their needs, not ours.  We put extra effort into a regular cadence of communication with the parents in the form of weekly emails and a current web site.  We used those emails to highlight kids’ performance and also let parents know what we’d be working on in practice that week.  We made sure that we rotated kids in the batting order so that everyone got to bad leadoff once and cleanup once.  We rotated kids so that almost every kid played half of each game in the infield and half in the outfield.  We took any and all requests from kids who wanted to play a specific position for a few innings.  Many of these basic principles – communicating well, a clear operating system, listening to stakeholders, a People First approach – are lessons learned from work as a CEO.

Proper expectations and a large dose of patience helped.  After the first couple games, we were 0-2, and I was very frustrated.  But I reminded myself that 7 and 8 year olds are just kids, and my frustration wasn’t going to help us achieve our objectives of having fun and learning the game.  So I recalibrated my expectations and took much more of a laid-back attitude.  For example, any time I saw one kid goofing off a little bit in practice, I gently got him or her back in line.  But when I saw multiple kids’ attention fading, I took it as a sign that whatever I was doing as a coach wasn’t working, called a break, and did something else.  This kind of “look in the mirror” approach is always helpful at work, too.

Reward and recognition were key.  We definitely adopted a Whale Done! approach with the kids.  We got the kids in the dugout fired up to cheer on batters.  First base coaches did big high fives, smiles, and literal pats on the back for every hit.  Post-game huddles and emails to parents focused on highlights and what went right for the kids.  One of my favorite moments of the season was when one player, who only had one hit all year and struck out almost every time at bat, had two hits, an RBI, and a run scored in our final game.  Not just the coaches, but the other kids and all the parents went absolutely BANANAS cheering for this player, and it brought huge smiles to all our faces.  I am 100% certain that the focus on the positive encouraged the kids to try their hardest all season, much as I believe that same philosophy encourages people to take risks and work hard at the office.

The biggest thing I take back to the workplace with me from the experience.  I was reminded about how powerful achieving a state of “flow,” or “relaxed concentration” is.  I recounted these principles in this blog post from a couple different books I’ve read over the years – Mihaly Csikszentmihalyi’s Flow and Tim Gallway’s Inner Game books – Golf, Tennis, and Work.  The gist of achieving a state of flow is to set clear goals that are stretch but achievable, become immersed in the activity, pay attention to what’s happening, and learn to enjoy immediate experience.  All leaders – in sports, business, or any walk of life – can benefit from this way of living and leading.

I loved every minute of coaching.  It helped that we ended up with a really strong record.  But more than that, building relationships with a bunch of great kids and great parents was fun and fulfilling and incredibly thankful and rewarding.  The “thank you ball” that all the kids autographed for me is now a cherished possession.  Working and getting extra time with my own two kids was the icing on the cake.  All I want to know is…is it time for next season yet?  I am ready!

This post is really for Coaches Mike, Paul, and Oliver; and players Emily, Casey, Lauryn, Mike, Josh, Holden, Hudson, Wilson, Drew, Kevin, Matthew, and Christian.

Apr 19 2006

Counter Cliche: I Know When I See One, Too

Counter Cliche:  I Know When I See One, Too

I haven’t written a counter to one of Fred’s VC Cliche’s of the Week for a while now, but today’s was too good to resist.  While I haven’t (and most entrepreneurs haven’t) worked with 200 VCs, I have seen, heard about, been one (sort of), and worked with enough of them to know enough to comment as follows:  as is the case with Fred and entrepreneurs, I’m not sure I can define what makes a great VC in one phrase, but I know one when I see one, and here are some of the characteristics they exhibit:

– Major pattern recognition — "I’ve seen this movie before, and I know how it ends…";
– Deep understanding of the market and/or customer set to add strategic value;
– Fundamental desire to be a product manager or marketing manager of your product, but also —
– Ability to stay out of the weeds with day-to-day details when the Board meeting ends;
– Always ready with a story or bon mot about other crazy investors or even crazier entrepreneurs to make you feel better about your own life;
– Complete transparency about the motives of his/her fellow GPs and LPs and ability/appetite for follow-on financings (and needless to say, no/limited blocking of transactions that are clearly in the company’s best interests but might run counter to his/her firm’s own short-term interests);
– Willingness to jump into a debate with the strongest of convictions, yet without 100% of the facts, since 100% of the facts are never available;
– Equal willingness to admit being wrong if a clear and compelling argument comes forth; and of course the most critical —
– No fear of yielding to Management when Management knows best!
– Note — note included — major rolodex (a nice to have, but not required)

The other part of the counter cliche is that I’m sure there are some great entrepreneurs who only exhibit a few of Fred’s list of traits…much as I’m sure there are some great VCs who only exhibit a few of my list above.

Feb 16 2025

Why Executive Searches are So Slow, and What You Can Do About That as a Candidate

It’s been a big break between posts – as many of you probably know, I moved to Board Chair and left the CEO role at Bolster last summer (it’s now in the very capable hands of my friend and co-founder Cathy Hawley), and I’m now CEO of a super cool AI company called Acrolinx.  So yes, that means I went through a job search – and I found my ultimate job as a result of an inbound cold email from a headhunter!  The rich irony in that as someone who founded an executive search platform is not lost on me.

So when a good friend of mine who is also between CEO gigs and looking at several opportunities asked me the other day “why is this process so slow, and what can I do about it?” I riffed with him on the theme for a bit and thought I’d share my thinking here. 

Why Executive Searches are Slow

My top three reasons on this are pretty varied – there’s no specific theme.

  1. Boards aren’t efficient hiring managers. When hiring a CEO, even the best intentioned boards can be slow to move. Frequently they operate with a search committee, and even if there’s a lead director on the search committee or even no actual search committee, by design they need to operate with a high degree of consensus. Organizing five calendars to meet with or debrief on a candidate can take weeks. And a single loud voice saying “no” or “not sure” can paralyze a board. All this is true for a CEO search but can also be true when a less experienced CEO is trying to hire a CXO and needs a lot of Board involvement in the process. At Bolster, we’ve worked on mitigating this by getting the key decision-makers aligned on search criteria at the beginning of the search, prepping interviewers, and creating a scorecard for each candidate that is visible to all decision-makers, but sometimes that doesn’t matter.
  2. Boards and CEOs often don’t know what they want.  Whether a company is hiring a role for the first time or replacing an executive, they often get to a generic job spec but don’t actually know what they’re looking for. Not all CEOs are created equal. Not all CROs have the same core competencies. At Bolster, we developed a description of role archetypes for each C-suite or Head-or role that helps with this process (eg for a CFO, do you want an Accounting type, a Finance/Ops type, or a Deal type?). But even if a Board or hiring CEO has this level of detail down, it can still be a murky picture, trapped between the company’s past successes and failures on one side and its future needs on the other. Processes move slowly because it take a while for the picture to become less murky – circumstances around the company evolve, or people see how the company operates without this role as others pick up the slack, and therefore the needs of the role shift or come into focus. Sometimes meeting a series of candidates is the only thing that can help drive this focus, and per the first bullet above, this just takes time. If a company has a strong search partner, that may speed things up via quick presentation of calibration candidates.
  3. There’s no precipitating crisis.  Most companies and departments, most of the time, are not in crisis. A lot of companies can operate without a given executive, even a CEO, for quite some time. Some things done (don’t) get done. Other people rise to the occasion and pick up the most important items. Or the company has hired an interim or fractional executive as a stop gap measure. Without a specific and clear sense of urgency, searches often don’t have a driving force. Sometimes there’s a precipitating crisis like a system outage or massive customer churn or the company running out of cash that can provide that driving force, but that is not the norm.

What Can You as a Candidate Do About It?

The answer is probably “not much.”  But if my own search was any indicator, I’d give you the same advice I give people internally at my company when they ask me how to get a promotion.  My answer is “start doing the job today, don’t wait to actually get the job.”  Obviously a candidate for a CEO role or any other executive role can’t actually start doing the job as an existing employee could start taking on additional pieces of work.  But there are a lot of things you can do to “act as it” and get the hiring Board or hiring CEO’s attention.  For example:

  • As a CEO candidate, be a management consultant.  Work on designing a strategy for the company you want to work for.  Do a tremendous amount of homework you can do from the outside – read analyst reports, get stealth demos, do market and customer interviews.  You don’t have to explain what you’re up to in terms of identifying the company.  You can say you’re interviewing for a CEO role in the sector.  Or even that you’re doing market research.  But proactively sending the hiring board a strategy deck and asking for the next meeting is a good way of differentiating yourself as a candidate and potentially accelerating a process.
  • As a CRO candidate, go try to sell the company’s product.  Do it to a couple “friendlies” (e.g, people who are friends of yours, not active customers or prospects of the company you’re interviewing with) so you don’t tread on the actual business.  But create your own deck.  Get meetings.  Write up your experience.  Sending the CEO or board an email that says “Hey, I have a prospect already in the final stage of the funnel for you, can we work together to close her?” is a sure way to differentiate yourself as a candidate and potentially accelerate a process.

There may be a macro answer here as well.  The market is still choppy, and boards and CEOs are more conservative in most sectors and subsectors than they are in go-go times.  So that may be slowing things down in general and may even make it harder to act as-if.  But that doesn’t mean you can’t try.

May 19 2011

Be Ruthless With Your Time

Be Ruthless With Your Time

I have historically been very open with my calendar.  For most of my career, people who want to meet with me, both internally or externally (with the exception of random vendor solicitation), generally have gotten to meet with me.  Some of this is generosity, but I’m also a compulsive networker and have always made time proactively to meet with people just to meet them, learn more about different pockets of the industry or finance, meet other entrepreneurs and find out what they’re up to or help them, and connect more broadly from there.  I’ve also routinely been on multiple boards at the same time, as I’ve found that’s a very helpful part of my management routine.

But of late, I’m struggling more and more with calendar management.  There are more and more demands on my time internally as Return Path gets bigger.  There are more asks from people with whom I really don’t want to meet.  More travel, which sucks up a lot time.  A longer commute and more people who I want to see at home who have early bedtimes.  So I’ve taken to being more ruthless with my time.  I could probably do an even better job at it than I am now.

The main shifts I’m trying to make are to be proactive instead of so reactive; to cut meetings, shrink them, or group them when appropriate internally; to use videoconferencing instead of travel where possible; and honestly to just be a little more selfish and guarded with my time.  If the meeting doesn’t have something in it for me or Return Path — some promise of learning something or meeting someone either directly or indirectly helpful — I’m unlikely to do it any more as I once would, or I’m pickier about it (it has to be in my office so I don’t have to travel…it can only be 30 minutes long, etc.).

The two main tools I’m trying to use to manage my calendar proactively, mostly driven my brilliant executive assistant Andrea, might be useful to others, so I thought I’d share them here.

The first one is a networking list.  Andrea and I created a simple spreadsheet of everyone externally that I like to keep in touch with, and we prioritized it.  Every time I meet with someone on it, we mark the date.  Then when we meet to review my calendar periodically, we look at the list and figure out who I should reach out to in order to set up the next wave of meetings.  (I have one for internal check-in meetings with people other than my direct reports as well.)

The second is a time allocation model.  I am sure I got this idea from David Allen or Jim Collins or some other author that I read along the way.  First, we are religious about keeping an accurate calendar, including travel time, and we even go back and clean up meetings after they’ve happened to make the calendar an accurate reflection of what transpired.  At the end of each quarter, we download the prior three months’ worth of meetings, we categorize them, and we see where my time went.  Then we make changes to the upcoming quarter’s calendar to match my targets based on what I’m trying to accomplish.  For what it’s worth, my categories have changed over time, but currently, they are Free, Travel, Non-Return Path, Internal, Board, Client/External.  Pretty high level.  This exercise has been really helpful in keeping me proactive and on track.

I miss some of the more random networking that I used to do.  I am at least a moderate believer in serendipity, and the likelihood of serendipity goes down as I clamp down on my calendar.  And I will miss being on some outside Boards or helping new entrepreneurs figure out how to be first time CEOs.  But hopefully my combination of being selectively proactive and exercising good judgment about what inbound things to jump on will keep the machine humming.