Counter Cliché:  And Founders, Too

This week, Fred’s chiche is that "the success of a company is in inverse proportion to the number of venture capitalists on the board".

I’d argue that the same statement is true of founders or management.

Boards help govern the company and watch out for shareholder interests.  Boards give outside perspectives and strategic advice to the company’s leadership.  Boards hire and fire the CEO.  And — more and more every day with large public companies — boards keep management honest.  How can these critical functions occur when a Board has too many members of the management team on it?  They can’t.  We’ve had outside directors at Return Path from Day 1.

I’m not advocating that Boards meet 100% apart from senior management.  On the contrary, our most productive Board meetings at Return Path are the ones where we have lots of management participation.  But execs present and discuss — and don’t vote — and they generally leave the last 30-60 minutes of every meeting for just the Board to discuss issues in private.  I’m also not advocating that CEOs don’t sit on boards or that the CEO never hold the Chairman role.  I think both of those items are critical to unify the watchdog function of looking out for all company stakeholders — shareholders, employees, and customers — at the highest level.

But while the success of a company may well be in inverse proportion to the number of venture capitalists on the board, that same success is jeopardized by too many execs, too.

That’s not just the title of a mediocre 1980’s sitcom starring Tony Danza, it’s a question I get periodically, including last week in an interview. A writer I know is working on an article on entrepreneurship and asked me, “Before you started your own business, how did you like working for other people?”

The question made me think a little bit. I know what she was asking — how I liked being the boss instead of working for one — but the way she phrased it is interesting and revealing about what it’s like to be a CEO. One of the biggest differences between being in a company and starting or running one is that you’re not working for a person, you’re working for many people.

As CEO of the company, I work for a Board and shareholders, I work for our customers, and I work for our employees. That’s how I approach the job, anyway.

Return Path’s Board of Directors is my boss, even though I’m one of the people on it. I report to the Board, and the Board is responsible for hiring and (hopefully not) firing the CEO, so technically, that’s my boss. The Board is also made up (for small private companies, anyway) of representatives of our biggest shareholders. As the main owners of the business, they are concerned with the growth, profitability, and overall health of the company, and they want to make sure we are building shareholder value day in, day out. That’s one very important perspective for me to have every day.

But I also work for our customers. I have to see myself as serving them — and more important, I have to steer the organization to believe that our customers are at the top of our food chain. If I do, then things will go well in the business. We will have the right products in the market at the right time to bring in new accounts. We will have a tremendous service delivery organization that wows customers and keeps them coming back for more. We will beat out our competition any day of the week. We will keep people paying our bills!

Most important, though, I work for our employees. This is very simple. An organization thrives because the people who make it up come to work inspired, focused, and productive. When they don’t, it doesn’t. I can’t wave a wand and make everyone happy all the time, but I try to focus a significant part of my time on making sure this is a great work environment; that the managers and executives are religiously focused on developing, managing, and motivating their teams; and that we’re doing a good job of communicating our mission, our values, and why each person’s job is important to the cause. This one’s the hardest of the three to get right, but it’s worth the effort.

Certainly, I don’t respond to each of my “bosses” every day as I would a direct supervisor, but in the long haul, I have to balance out the needs and interests of all three constituencies in order to have the organization be successful.

I’ve posted a lot over the years about feedback in all forms, but in particular how much I benefit from my 360 reviews and any form of “upward” feedback.  I’ve also posted about running a 360 process for/with your Board, modeled on Bill Campbell’s formula from Intuit.

I have a lot of institutional investors in our cap table at Return Path.  I was struck this week by two emails that landed in my inbox literally adjacent to each other.  One was from one of our institutional investors, sharing guidelines and timetables for doing CEO reviews across its portfolio.  The other was from one of our other institutional investors, and it invited me to participate in a feedback process to evaluate how well our investor performs for us as a Board member and strategic advisor.  It even had the Net Promoter Score question of would I recommend this investor to another entrepreneur!

The juxtaposition gave me a minute to reflect on the fact that over the 18 years of Return Path’s life, I’ve been asked to participate in feedback processes for Board members a few times, but not often.  Then I went to the thought that all of my reviews over the years have been self-initiated as well.  Just as it can be easy for a CEO to skip his or her review even when the rest of the company is going through a review cycle, it can be easy for investors to never even think about getting a review unless they get one internally at their firms.  I suspect many CEOs are reviewed by their Board, if not formally, then informally at every quarterly Board meeting.

It’s unfortunately a rare best practice for a venture capitalist or any other institutional investor to ask for CEO feedback.  I bet the ones who ask for it are probably the best ones in the first place, even though they probably still benefit from the feedback.  But regardless, it is good to set the tone for a portfolio that feedback is a gift, in all directions.

Running a Productive Offsite

A couple OnlyOnce readers asked me to do a post on how I run senior team offsites.  It’s a great part of our management meeting routine at Return Path, and one that Patrick Lencioni talks about extensively in Death by Meeting (review, book) – a book worth reading if you care about this topic.

My senior team has four offsites per year.  I love them.  They are, along with my Board meetings, my favorite times of the year at work.  Here’s my formula for these meetings:

–          WHY:  There are a few purposes to our offsites.  One for us is that our senior team is geographically distributed across 4 geographies at the executive level and 6 or 7 at the broader management team level.  So for us, these are the only times of the year that we are actually in the same place.  But even if we were all in one place, we’d still do them.  The main purpose of the offsite is to pull up from the day-to-day and tackle strategic issues or things that just require more uninterrupted time.  The secondary purpose is to continue to build and develop the team, both personal relationships and team dynamics.  It’s critically important to build and sustain deep relationships across the Executive Team.  We need this time in order to be a coordinated, cohesive, high trust, aligned leadership team for the company.  As the company has expanded (particularly to diverse geographies), our senior team development has become increasingly critical

–          WHO:  Every offsite includes what we call our Executive Committee, which is for the most part, my direct reports, though that group also includes a couple C/SVP titled people who don’t report directly to me but who run significant parts of the company (7-8 people total).  Two of the four offsites we also invite the broader leadership team, which is for the most part all of the people reporting into the Executive Committee (another 20 people).  That part is new as we’ve gotten bigger.  In the earlier days, it was just my staff, and maybe one or two other people as needed for specific topics

–          WHERE:  Offsites aren’t always offsite for us.  We vary location to make geography work for people.  And we try to contain costs across all of them.  So every year, probably 2 of them are actually in one of our offices or at an inexpensive nearby hotel.  Then the other 2 are at somewhat nicer places, usually one at a conference-oriented hotel and then one at a more fun resort kind of place.  Even when we are in one of our offices, we really treat it like an offsite – no other meetings, etc., and we make sure we are out together at dinner every night

–          WHEN:  4x/year at roughly equal intervals.  We used to do them right before Board meetings as partial prep for those meetings, but that got too crowded.  Now we basically do them between Board meetings.  The only timing that’s critical is the end of year session which is all about budgeting and planning for the following year.  Our general formula when it’s the smaller group is two days and at least one, maybe two dinners.  When it’s the larger group, it’s three days and at least two dinners.  For longer meetings, we try to do at least a few hours of fun activity built into the schedule so it’s not all work.

–          WHAT:  Our offsites are super rigorous.  We put our heads together to wrestle with (sometimes solve) tough business problems – from how we’re running the company, to what’s happening with our culture, to strategic problems with our products, services and operations.  The agenda for these offsites varies widely, but the format is usually pretty consistent.  I usually open every offsite with some remarks and overall themes – a mini-state-of-the-union.  Then we do some kind of “check-in” exercise either about what people want to get out of the offsite, or something more fun like an envisioning exercise, something on a whiteboard or with post-its, etc.  We always try to spend half a day on team and individual development.  Each of us reads out our key development plan items from our most recent individual 360, does a self-assessment, then the rest of the team piles on with other data and opinions, so we keep each other honest and keep the feedback flowing.  Then we have a team development plan check-in that’s the same, but about how the team is interacting.  We always have one or two major topics to discuss coming in, and each of those has an owner and materials or a discussion paper sent out a few days ahead of time.  Then we usually have a laundry list of smaller items ranging from dumb/tactical to brain-teasing that we work in between topics or over meals (every meal has an agenda!).  There’s also time at breaks for sub-group meetings and ad hoc conversations.  We do try to come up for air, but the together time is so valuable that we squeeze every drop out of it.  Some of our best “meetings” over the years have happened side-by-side on elliptical trainers in the hotel gym at 6 a.m.  We usually have a closing check-out, next steps recap type of exercise as well.

–          HOW:  Lots of our time together is just the team, but we usually have our long-time executive coach Marc Maltz from Triad Consulting  facilitate the development plan section of the meeting.

I’m sure I missed some key things here.  Team, feel free to comment and add.  Others with other experiences, please do the same!

Drawing the LineWe are having a bit of a debate at the moment internally around our Sender Score deliverability business about how to handle clients who are in businesses that are, shall we say, not exactly as pure as the driven snow.  As a company that provides software and services to businesses without a vertical focus, we are often approached by all sorts of companies wanting our services where we don’t love what they do.  Examples include:

Gambling
Tobacco
Neutriceuticals
Guns
Adult content or products

Our challenges are along three dimensions, each of which is a little different.  But common threads run through all three dimensions. 

Dimension 1:  Our deliverability technology platform.   Our basic technology is used by mailers of all shapes and sizes to preview their campaigns, monitor their deliverability, and analyze their reputation metrics.  It doesn’t deploy campaigns.  Do we care who the users are?

Dimension 2:  Our full service deliverability practice that comes with consulting and high-touch account management.  This service offering has an additional layer of complexity in that our employees work closely with accounts and their web sites.  We already allow employees to opt-out of accounts where they find the work objectionable.  But is that enough?

Dimension 3:  Our whitelist, Sender Score Certified. This one is even trickier.  On the one hand, our program has fairly clear, published standards.  We do a thorough qualitative check of the client’s web site and email program to make sure, among other things, that the program is opt-in.  We monitor the client’s quantitative reputation metrics in real-time to make sure its complaint rate is low, signifying that its customers like (or at least don’t mind) receiving its email.  On the other hand, this program is supposed to signify the best of the best for email marketing and newsletters, which is why it’s used by so many ISPs and filters as their standard for defining “good mail.”  And yet on a third hand (perhaps there’s some sort of herbal remedy that can help me with that problem), for many ISPs, our program is their only whitelist, so clients who are above board, even if in a grey industry, may have no other option.

So is it our place to legislate morality, or should we just focus on what’s legal and what’s not legal?  How much accountability do clients bear for content that shows up in their emails from advertisers?  For example, and I’m making this up, what do we do if a men’s health magazine that’s a client has links in its email newsletters that are placed by an affiliate network that click through to a pornography site?  What if the pornography in question is legal in one country but not another?  How much time and energy should we spend vetting clients before we take them on?  Or monitoring them around these issues once they’re a client?  Does it matter which product they’re using?

I’d love feedback from the outside world (or the inside world) on how we should think about and handle these issues.

Pret a Manager

My friend James is the GM of the Pret a Manger (a chain of about 250 “everyday luxury” quick service restaurants in the UK and US) at 36th and 5th in Manhattan.  James recently won the President’s Award at Pret for doing an outstanding job opening up a new restaurant.  As part of my ongoing effort to learn and grow as a manager, I thought it would be interesting to spend a day shadowing James and seeing what his operation and management style looked like for a team of two dozen colleagues in a completely different environment than Return Path.  That day was today.  I’ll try to write up the day as combination of observations and learnings applied to our business.  This will be a much longer post than usual.  The title of this post is not a typo – James is “ready to manage.”

1. Team meeting.  The day started at 6:45 a.m. pre-opening with a “team brief” meeting.  The meeting only included half a dozen colleagues who were on hand for the opening, it was a mix of fun and serious, and it ended with three succinct points to remember for the day.  I haven’t done a daily huddle with my team in years, but we do daily stand-ups all across the company in different teams.  The interesting learning, though, is that James leaves the meeting and writes the three points on a whiteboard downstairs near the staff room.  All staff members who come in after the meeting are expected to read the board and internalize the three points (even though they missed the meeting) and are quizzed on them spontaneously during the day.  Key learning:  missing a meeting doesn’t have to mean missing the content of the meeting.

2. Individual 1:1 meeting.  I saw one of these, and it was a mix of a performance review and a development planning session.  It was a little more one-way in communication than ours are, but it did end up having a bunch of back-and-forth.  James’s approach to management is a lot of informal feedback “in the moment,” so this formal check-in contained no surprises for the employee.  The environment was a little challenging for the meeting, since it was in the restaurant (there’s no closed office, and all meetings are done on-site).  The centerpiece of the meeting was a “Start-Stop-Continue” form.  Key learning:  Start-Stop-Continue is a good succinct check-in format.

3. Importance of values.  There were two forms of this that I saw today.  One was a list of 13 key behaviors with an explanation next to each of specific good and bad examples of the behavior.  The behaviors were very clear and were “escalating,” meaning Team Members were expected to practice the first 5-6 of them, Team Leads the first 7-8, Managers the first 10, Head Office staff the first 12, Executives all 13 (roughly).  The second was this “Pret Recipe,” as posted on the public message board (see picture below).  Note – just like our values at Return Path, it all starts with the employee.  One interesting nugget I got from speaking to a relatively new employee who had just joined at the entry level after being recruited from a prominent fast food chain where he had been a store general manager was “Pret really believes this stuff — no lip service.”

I saw the values in action in two different ways.  The first was on the message board, where each element of the Pret Recipe was broken out with a list of supporting documents below it, per the below photo.  Very visual, very clear.

The second was that in James’s team meeting and in his 1:1 meeting, he consistently referenced the behaviors.  Key learning:  having values is great, making them come to life and be relevant for a team day-in, day-out is a lot harder but quite powerful when you get it right.

4. Managing by checklist.  I wrote about this topic a while ago here, but there is nothing like food service retail to demand this kind of attention to detail.  Wow.  They have checklists and standards for everything.  Adherence to standards is what keeps the place humming.  Key learning:  it feels like we have ~1% of the documentation of job processes that Pret does, and I’m thinking that as we get bigger and have people in more and more locations doing the same job, a little more documentation is probably in order to ensure consistency of delivery.

5. Extreme team-based and individual incentive compensation.  Team members start at $9/hour (22% above minimum wage that most competitors offer).  However, any week in which any individual store passes a Mystery Shopper test, the entire staff receives an incremental $2/hour for the whole week.  Any particular employee who is called out for outstanding service during a Mystery Shop receives a $100 bonus, or a $200 bonus if the store also passes the test.  The way the math works out, an entry level employee who gets the maximum bonus earns a 100% bonus for that week.  But the extra $2/hour per team member for a week seemed to be a powerful incentive across the board.  Key learning: team-based incentive comp is something we use here for executives, but maybe it’s worth considering for other teams as well.

6. Integrated systems.  Pret has basically one single software system that runs the whole business from inventory to labor scheduling to finances.  All data flows through it directly from point of sale or via manager single-entry.  All reports are available on demand.  The system is pretty slick.  There doesn’t seem to be much use of side systems and side spreadsheets, though I’m sure there are some.  Key learning: there’s a lot to be said for having a little more information standardized across the business, though the flip side is that this system is a single point of failure and also much less flexible than what we have.

7. Think time.  I’ve written a little about working “on the business, not in the business,” or what I call OTB time, once before, and I have another post queued up for later this summer about the same.  Brad Feld also very kindly wrote about it in reference to Return Path last week.  Working in retail means that time to work on IMPORTANT BUT NOT URGENT issues is extremely hard to come by and fragmented.  I suspect that it comes more at the end of the day for James, and it probably comes a lot more when he doesn’t have someone like me observing him and asking him questions.  But his “office” (below), exposed to the loud music and sounds and smells of the kitchen, certainly doesn’t lend itself to think time!  Key learning:  of course customers come first, but boy is it critical to make space to work OTB, not just ITB.  Oh, and James needs a new chair that’s more ergonomically compatible with his high countertop desk.

Years ago, I spent a few weekends working in my cousin Michael’s wine store in Hudson, NY, and I wrote up the experience in two different posts on this blog, the first one about the similarities between running a 2-person company and a 200-person company, and the second one about how in a small business, you have to wear one of every kind of hat there is.  My conclusion then was that there are more similarities than differences when it comes to running businesses of different types.  My conclusion from today is exactly the same, though the focus on management made for a very different experience.

Thanks to James, Gustavo, Orlanda, Shawona, and the rest of the team at the 36th & 5th Pret for putting up with the distraction of me for the bulk of the day today — I learned a lot (and particularly enjoyed the NYC Meatball Hot Wrap) and now have to figure out how to return the favor to you!

Startup CEO (OnlyOnce- the book!), Part II – Crowdsourcing the Outline

As I mentioned a few weeks ago here, I’m excited to be writing a book called Startup CEO:  A Field Guide to Building and Running Your Company, to be published by Wiley & Sons next summer.  Since many readers of OnlyOnce are my target audience for the book, I thought I’d post my current outline and ask for input and feedback on it.  So here it is, still a bit of a work in progress.  Please comment away and let me know what you think, what’s missing, what’s not interesting!

1           Part One: Vision and Strategy (Defining the Company)
1.1          Setting the Company’s Agenda
1.2          NIHITO! (or, “Nothing Interesting Happens in the Office”)
1.3          Setting the Business Direction
1.4          Strategic Planning, Part I: Turning Concepts Into Strategy
1.5          Strategic Planning, Part II: Creating the Plan
1.6          Defining Mission, Vision and Values
1.7          Communicating Vision and Strategy
1.8          The Role of M&A
1.9          The Art of the Pivot
1.10       How Vision and Strategy Change over Time

2           Part Two: Talent (Building the Company’s Human Capital)
2.1          Building a Team
2.2          Scaling the Team
2.3          Culture
2.4          Interviewing
2.5          Recruiting
2.6          Onboarding
2.7          Setting Goals
2.8          Feedback
2.9          Development
2.10       Compensation
2.11       Promoting
2.12       Rewarding
2.13       Managing Remote Offices and Employees
2.14       Firing: When It’s Not Working
2.15       How Talent Changes over Time

3           Part Three: Execution (Aligning Resources with Strategy)
3.1          Making Sure There’s Enough Money in the Bank
3.2          Types of Financing
3.3          Fundraising Basics
3.4          Negotiating Deals
3.5          Pros and Cons of Outside Financing
3.6          Forecasting and Budgeting
3.7          Creating a Company Operating System
3.8          Meeting Routines
3.9          Driving Alignment
3.10       A Metrics-Driven Approach to Running a Business
3.11       Learning
3.12       Post-Mortems
3.13       Thinking About Exits
3.14       How Execution Changes over Time
3.14.1      Finance
3.14.2      Execution

4           Part Four: Management And Leadership (The How of Being a CEO)
4.1          Leading an Executive Team
4.2          Critical Personal Traits
4.3          Being Collaborative
4.4          Being Decisive: Balancing Authority and Consensus
4.5          The Value of Symbolism
4.6          Getting the Most out of People
4.7          Diving Deep without Being Disruptive
4.8          Articulating Purpose
4.9          Collecting Data from the Organization
4.10       Managing in an Economic Downturn
4.11       Managing in Good Times vs. Bad Times
4.12       Communication
4.12.1      Macro (to Your Company and Customers)
4.12.2      Micro (One-on-One)
4.13       How Management and Leadership Change over Time

5           Part Five: Boards (A Unique Aspect of the CEO’s Job)
5.1          Building Your Board
5.2          Meeting Materials
5.3          Meetings
5.4          Between Meetings
5.5          Making Decisions and Maximizing Effectiveness
5.6          The Social Aspects of Running a Board
5.7          Working with the Board on Compensation
5.8          Evaluating the Board
5.9          Serving on Other Boards
5.10       How Boards Change over Time

6           Part Six: Managing Yourself So You Can Manage Others
6.1          Creating a Personal Operating System
6.2          Working with an Executive Assistant
6.3          Working with a Coach
6.4          Finding Your Voice
6.5          The Importance of Peer Groups
6.6          Your Family
6.7          Taking Stock
6.8          Staying Fresh
6.9          Staying Healthy
6.10       Traveling

I realize I haven’t posted much lately.  As you may know, the title of this blog, OnlyOnce, comes from a blog post written by my friend and board member Fred Wilson from Union Square Ventures entitled You Are Only a First-Time CEO Once, which he wrote back in 2003 or 2004.  That inspired me to create a blog for entrepreneurs and leaders.  I’ve written close to 1,000 posts over the years, and the book became the impetus for a book that another friend and board member Brad Feld from Foundry Group encouraged me to write and helped me get published called Startup CEO:  A Field Guide to Scaling Up Your Business back in 2013.

Today is a special day in my entrepreneurial journey and in the life of the company that I started back in 1999 (last century!), Return Path, as we announce that Return Path has entered into a definitive agreement to be acquired by an exciting new company called Validity.  Press release is here.

Over almost 20 years, we’ve built Return Path into one of the largest and (I think) most respected companies in the email industry.  We’ve had a culture of innovation that has led to some groundbreaking products for our customers and partners to help make email marketing work better for consumers as well as marketers, and to help keep inboxes safe and clean for mailbox providers and security companies.  

But the company is unusual in many respects.  One of those is longevity. I’m not sure how many Internet companies started in 1999 are still private, backed and led by the same team the whole time, and generally in the same business they started in.  Another is our values-driven “People First” culture. From Day 1, we have believed that if we attract and retain and develop and invest in the best people, we will make our customers successful with great products and service, and that if we do right by our customers, we will do right long term by our shareholders.  While I know that not every employee who ever walked through our doors had a great experience, I know most did and hope that all of them realize we tried our best. Finally, I’m proud that our company gave birth to a non-profit affiliate Path Forward a few years back at the hands of executives Andy Sautins, Cathy Hawley, and Tami Forman.  Path Forward helps parents get back to work after a career break and helps companies improve their gender diversity and hiring biases and has already been a game changer for dozens of companies and hundreds of women.

Today, Return Path serves almost 4,000 customers in almost every country on the globe, with $100 million in revenue, profitable, and excited about the next leg of our brands’ and our products’ lives in the care of Validity.  If you haven’t heard of Validity before today, watch out – you will hear a LOT about them in the weeks and months ahead. They are an incredibly exciting new company with a vision to help tens of thousands of companies across the globe improve their data quality but also help them use data to improve business results.  That vision, inspired by a new friend, CEO Mark Briggs, is a wonderful fit for Return Path’s products and services and people.

To finish this post where I started, Fred’s exact words in that post which got this blog going were:

What does this mean for entrepreneurs and managers? It means that the first time you run a business, you should admit what you are up against. Don’t let ego get in the way. Ask for help from your board and get coaching and mentoring. And recognize that you may fail at some level. And don’t let the fear of failure get in the way. Because failure isn’t fatal. It may well be a required rite of passage.

All of that is true and has been great advice for me over the years.  But Fred left out one important piece, which is that entrepreneurs need to constantly thank the people around them who either work their butts off as colleagues in the business or who give them helpful advice and coaching.  Return Path’s journey has been a long one, longer than most, and the full list of people to thank is too long for a blog post.

I’ve noted Fred and Brad in this post already and I want to thank them and also thank Greg Sands from Costanoa Ventures, the third member of our “dream team” investor syndicate, for their friendship and unwavering support and good counsel for me and Return Path for almost two decades, as well as many other board members we’ve had over the years including long-time independent directors Jeff Epstein, Scott Petry, and Scott Weiss.

I want to thank my co-founders Jack Sinclair and George Bilbrey, and anyone who has ever been on my executive team, including long-time execs Ken Takahashi, Shawn Nussbaum, Cathy Hawley, Dave Wilby, Anita Absey, Angela Baldonero, Andy Sautins, Louis Bucciarelli, Mark Frein, and David Sieh.  There’s nothing quite like being in the proverbial foxhole with someone during a battle or two or ten to forge a tight bond. I want to thank Andrea Ponchione, my extraordinary assistant for 14 years, who keeps me running, sane, and smiling every day. I want to thank my executive coach Marc Maltz and the members of my CEO Forum for allowing me to be unplugged and for their friendship and advice.  I want to thank all of Return Path’s 430 employees today and over 1,300 ever for their hard work in building our company and culture together and for our 4,000 customers and partners for putting their faith in us to help them solve some of their biggest challenges with email.

Finally, no thank you list for this journey would be complete without saying a special thank you to my wonderful wife Mariquita and kids Casey, Wilson, and Elyse.  They deserve some kind of special honor for being inspirational cabin-mates on the entrepreneurial roller coaster without ever being asked if they were up for it.

This event may inspire me to begin writing more regularly again on OnlyOnce.  Stay tuned!

(This post also appeared on Bolster.com).

As we wrote in The Gig Economy Executive, the major societal trend to “gig,” or part-time/freelance work, has reached the C-Suite.  We created Bolster to help organize a talent marketplace out of what is mostly an informal economy today – one where VC- and PE-backed companies find trusted freelance executives and consultants from their networks.  

In that earlier blog post, we wrote about the different types of on-demand executive work that C-level executives engage in:  interim, fractional, mentor/coach/advisor, project-based consulting, and board roles.

As we’ve been building Bolster this year, we’ve come to appreciate that not only are there different types of gig economy roles…there are several different archetypes of gig economy executives, too.  While there is a clear common theme of the desire to do some form of freelance, or non-full-time work that cuts across the four types, they are very different in their stage of life and their needs.  These are our four main Member user personae, to use the language of Product Management.

First, there is the In Between Executive.  This is the original concept of our founding investors at High Alpha and Silicon Valley Bank that drove their interest in Bolster.  The In Between Executive is someone who is generally mid-career and used to working in full time C-level roles and is, for whatever reason, between jobs at the moment.  Maybe her company just got acquired and she is taking a break.  Maybe her company restructured her out of a job.  Maybe she needed or wanted to take a break from work for family or health reasons.  Maybe she was just ready to look for a new career challenge.  The In Between Executive is perfectly suited to any of the on-demand executive role types but is a particularly good fit for interim CXO, mentor/coach/advisor, and project-based consulting roles.

Second, there is the Career On-Demand Executive.  The Career On-Demand Executive is usually someone who has had many years of experience as a full-time executive and who is now looking for something more flexible, or who just enjoys more variety in his work.  One of the Career On-Demand Executives in the Bolster network I spoke with early on described her journey to me like this:  she was “between things” when a friend of hers who had moved to France and started a company asked her to come set up her HR Department and run it for 6 months while hiring full-time staff.  She took a month off, lived in Paris for 6 months, took another month off, then started to look for something else like that.  Ooh la la.  Sounds pretty good to me.  The Career On-Demand Executive is a particularly good fit for interim CXO, fractional CXO, and project-based consulting roles.

Next, there is the Not Retired Executive.  When I think of the Not Retired Executive, I think of my Dad, who was a successful technology entrepreneur for 30+ years.  Since he sold his company several years back, he has helped a number of startup CEOs do everything from raise money to build a sales and marketing plan, to manage supply chains.  Sometimes he gets paid in cash as a consultant, sometimes he gets equity as an Executive Chairman.  Sometimes he talks to younger entrepreneurs and helps them out “just because.”  The reality of the Not Retired Executive today, however, is that many people are “not retiring” younger and younger because they’ve made enough money to take a step back from hard-charging full-time jobs.  The Not Retired Executive is perfectly suited to any of the on-demand executive role types.  The ones who are later in their careers and closer to being actually retired are particularly good fits for mentor/coach/advisor and board roles.

Finally, there is the Side Hustle Seeker.  The Side Hustle Seeker is someone who is a full-time executive somewhere but who is looking for additional professional opportunities.  She may be an experienced CMO who is excited about mentoring up-and-coming marketing leaders via a local or industry-based professional organization.  She may be looking for chances to “pay it forward” because someone mentored her along the way, earlier in her career.  She may have accumulated enough experience and wisdom to be ready for her first board of directors seat.  Regardless, she’s someone who is a “high wattage” professional who wants to learn and grow herself by connecting with others outside her day-to-day role.  The Side Hustle Seeker is best matched with mentor/coach/advisor and board roles.

So, what kind of gig economy executive are you, and how can Bolster help you find the kind of work you’re looking for while providing you with tools and resources to simplify your life?  Join Bolster as a member to find out!

(This is the third in a series of three posts on this topic.)

In previous posts (here, here) , I talked about the difference between Mentors and Coaches and also how to select the right ones for you. Once you’ve selected a Mentor or Coach, here are some tips to get the most out of your engagement.

Starting to work with a CEO Mentor is fairly easy. Give them some materials to help understand your business, and then come prepared to every session with a list of 1-2 topics that are keeping you up at night where you want to benefit from the person’s experience.

Kicking off a CEO Coach engagement is more in-depth. I always recommend starting to work with a CEO Coach by doing a DEEP 360.  Not one that’s a bland anonymous survey instrument, but one that involves the Coach doing 15-20 in-depth interviews with a wide range of people from team to Board to others in the organization to people you’ve worked with outside the organization, including some non-professional contacts.  Let the Coach really learn about you from others.  The reason for this is that, although you may have an area of development that you want to focus on (like I did when I met Marc), you may actually need help in other areas a lot more acutely.

In general,  I’d say these are a few good rules of thumb for getting the most out of your Coach or Mentor relationship and sessions of work together:

• Do your homework.  If you have an assignment to read an article, take a survey, or just write something up, either do it or cancel the next meeting or it will be a waste of everyone’s time
• Be present.  Step away from your desk. Turn off email.  Silence your phone.  These are some of the most valuable times for your own personal development and growth, and they are few and far between when you get to be a CEO.  Treasure them
• Bring your whole self.  Even if your coach is a full 5 on the Shrink-to-Management Consultant scale I mentioned above, people are people, and you’re no exception.  You have a bad day at home — it will show through at work and it will impact your Coach conversations (maybe less so your Mentor ones).  Don’t ignore it.  Mention it up front
• Don’t bullshit.  You know when you’re wrong about something or have made a mistake.  You may or may not be great about admitting it publicly, or even admitting it to yourself.  ADMIT IT TO YOUR COACH.  Otherwise, why bother having one?
• Encourage primary data collection.  The biggest place I’ve seen coaching relationships fail is when the Coach or Mentor only has access to a single point of information about what’s happening in the organization — you.  Even if you’re not in full-on 360 mode, encourage your Coach or Mentor to spend time with others in the organization or on your board here and there and have a direct line of communication with them.  If they don’t and all they’re working off is your perspective on situations, their output will be severely limited or subject to their own conjecture.  Especially if you can’t get the prior bullet point right (garbage in, garbage out!)
• Make it your agenda even if it means changing on the fly.  You may be working on an analysis of your team’s Myers-Briggs profile with your Coach – and that’s the topic of your next meeting – but right before the meeting, you learn that one of your CXOs is resigning.  Change the agenda.  It’s ok.  It’s your time, make it work for you
• Learn to fish.  At the end of the day, a good CEO Coach should offer you ways of thinking about things, ways of being, ways of learning in your organization, processes to give you the ability to do some elements of this by yourself – not just answering questions for you.  Sports trainers are useful for an athlete’s entire career to push them harder in workouts, but they also teach athletes how to work out on their own
• Reality check the advice.  Make sure to test the strategies that Coaches or Mentors are giving you against your organization.  All strategies won’t work in all organizations.  These conversations should offer a variety of strategies – you can pick one or pick none and do something totally different.  The value isn’t in being told what to do, it is in going through the process of deciding what to do for YOUR organization with some expert inputs and reflections on other experiences
• Close the loop.  I’ve written before about how to solicit feedback as a CEO.  To make sure your coaching work is effective, be sure to include feedback loops with your key stakeholders (team and board) on the things you’re working on with your CEO Coach

It’s worth the money.  CEO Coaches can be really expensive.  Like really, really expensive.  $500-1,500/hour expensive.  CEO Mentors can be free and informal, but sometimes they charge as well or ask for advisor equity grants.  Even if you have a thin balance sheet, don’t be shy about adding the expense, and you shouldn’t pay for this personally.  Adding 10-20% to the cost of your compensation will potentially make you twice as effective a CEO.  If your board doesn’t support the expense…well, then you may have a different problem.

There’s a lot written publicly about this topic.  Jason Lemkin at SaaStr has a particularly good post that really puts a fine point on it.  And the coaching team at Beyond CEO Coaching a new boutique coaching firm specializing in coaching black CEOs, writes in “Who are you not to be great?”, “You can play it safe and reduce your risks and likely the rewards, or you can go big.  We at Beyond CEO Coaching want to help you to go big.”

By the way, this entire framework applies to non-CEOs as well.  Every professional would benefit from having a Coach and a Mentor in their life, even if those aren’t paid consultants but more senior colleagues or members of the company’s People Team.  Sometimes a Mentor and a Coach are one and the same…sometimes they are not.

Thanks to a large number of Bolster members I know personally who are CEO Coaches and Mentors for reviewing these posts — Chad Dickerson, Bob Cramer, Tim Porthouse, Marc Maltz, Lynne Waldera, Dave Karnstedt, and Mariquita Blumberg.

(Post 1 of 4 in the series on Scaling CROs)

In most startups, the founder is the first salesperson and while it may be difficult to let that go you’ll eventually scale, add sales reps, or maybe some form of a Sales Manager once there are more than a couple of reps.  In Startup CXO our Return Path CRO, Anita Absey, wrote about the journey of startup sales, from “selling on whiteboard” to “selling with PowerPoint” to “selling with PDF.” I encourage you to read that section if you’re wondering about hiring a CRO, but all of the hiring of sales reps and (possibly) a sales manager happens during what Anita calls the “White Board” stage as you’re beginning to transition to “Selling with PowerPoint.” 

Selling from a White Board means that you are essentially working with an interested potential customer on a custom and conceptual sale; selling from PowerPoint means that you are selling tailored solutions—you’re no longer at the discovery stage. Selling from either the White Board or Powerpoint stage is fine for an early-stage company, but eventually you’ll want to scale and hire your first CRO. Here are some of the telltale signs that will help you figure out if you should bring in a CRO.

First, you’ll know it’s time to hire a CRO when you’re nervous about HOW you’re going to make this quarter’s number — not just that WHETHER or not you’ll make it (since you should know that as much as anyone). Another sign that it’s time to hire a CRO is when you aren’t clear what the levers are, or what the pipeline/forecast details are, to hit those quarterly numbers. 

If you are spending too much of your own time managing individual deals and pricing, or teaching individual reps how to get jobs done, that’s a clear indicator that a CRO is needed. If your board asks you if you’re ready to step on the gas and scale your revenue engine (e.g., move from Powerpoint to PDF), and you don’t have a great answer and aren’t sure how to get to one then you need to hire a CRO.

A fractional CRO can add a lot of value, especially at a small volume where a full-time CRO would be overkill. Or, if your sale is very complex or to a very senior buyer, and a more junior sales team needs a fair amount of deal support from above, a fractional CRO makes a lot of sense. Sometimes a fractional CRO can help you enter a new adjacent segment (e.g., mid-market going to enterprise), and then you’ll need a seasoned professional to help translate sales processes from one segment to the other while keeping the initial segment running smoothly. 

If you’re not sure what kind of sales leader you’ll need long-term and full time because you’re not at enough scale yet, a fractional CRO can help you “try before you buy.” You can try out a specific type of revenue leader to see if that type works, for example, sales only, sales + customer success, manager of hunters, or builder of a high velocity sales engine, to name a few different options.

Hiring a CRO will definitely free up time for founders and allow them to work on other things that drive the business, without worrying about sales.

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