I’ve gotten to know a number of Bolster members over the last few years, and one who I have come to appreciate quite a bit is Tim Porthouse. I’m on Tim’s email list, and with his permission, I’m reprinting something he wrote in his newsletter this month on the topic of CEO engagement in politics and current events. As you may know, I’ve written a bunch on this topic lately, with two posts with the same title as this one, Should CEOs wade into Politics (part I here, part II here). Thanks to Tim for having such an articulate framework on this important subject.

Your Leadership Game: “No Comment.”

Should you speak up about news events/ politics?

Most of the time, I say, no!

Startup CEOs feel pressure to speak up on news events: Black Lives Matter, Abortion, LBGTQ+ rights, the conflict in Israel/Palestine, Trump vs. Biden. Many tell me they feel pressured to say something, but are deeply conflicted.

Like you, I am deeply distressed by wars, murder, restrictions on human rights, bias, and hate. But if we feel something, should we say something?

Before you speak up, ask the following questions:

1.      Mission relevance. Is your startup’s success or mission on the line? Are customers or employees directly impacted? Example: It makes sense for Airbnb to advocate when a city tries to ban short-term rentals. It makes sense to advocate for your LBGTQ+ employees when a state tries to restrict their rights.

2.      Moving the needle. Will speaking out change anything? If you “denounce” something or “take a stand,” what really happens? Example: If you have employees in a state banning abortion and you tell them your startup will support them as much as the law allows, this could create great peace of mind for employees. But if your startup does not operate in Ukraine or Russia, then denouncing Russia does little (and Russia does not care!)

3.      Expertise. Do you have a deep understanding of the situation? It’s usually more complicated than it appears, especially at first. Once you speak out, you have painted yourself into a corner you will be forced to defend.

4.      Precedence and equivalence. If you issue a statement about today’s news event, will you react to tomorrow’s event? Why not? Where do you draw the line?Someone will be offended that you spoke up about X but not Y.

5.      Backlash. Are you ready to spend significant time engaging with those who disagree with you?It can get ugly quickly, and mistakes can be costly. Plus, the American public is tiring of business leaders commenting on the news.

6.      Vicarious liability. Who are you speaking for? When you say, “Our startup denounces X”?Does the whole company denounce it? You don’t know, and probably not. Does the Leadership Team? They may feel pressured to support you. What you are really saying is, “I denounce X!” OK, great, then say it to your friends and family. Leave your startup to talk about business.

If your answers are “yes,” – then speak out.

If not, I recommend keeping quiet.

In my opinion, our job is to build great companies, not debate current events.

By not speaking out, you can say, “We don’t talk politics here.” You can shut down any two-sided arguments at work and say, “Let’s get back to work,”removing a big distraction. Remember when employees protested because Google was bidding for Pentagon contracts?

I realize that you will be challenged to make a statement, that, “Saying nothing is unacceptable/ complicit.” But whoever challenges you will only be satisfied if you support their view.

If you still want to speak out, I respect your choice. Some of you will be angry with me for writing this, and I accept that. I’m asking you to think carefully before you make a statement.

(This is the third post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  First two posts are here and here.)

Friday, March 20, Day 4

• Morning pilates going pretty well, a good daily routine here
• Wellness Screening on the way in for the first time.  Uniformed National Guard guys taking temperature on surface of face/temples.  Can’t get it to work – takes 6x
• Leadership and prioritization of important over urgent – staff the team
• Strategic National Stockpile failure – they send us 60,000 masks and Colorado is using 68,000/day.  They send us ZERO ventilators. Seems like it’s neither strategic nor a stockpile. Guess it really is every state for itself
• Unclear sometimes what the actual role of the state is – sometimes procuring, sometimes getting private sector to procure with some coordination, etc.
• Getting out in front of the parade – the private sector is swarming all over this, how can we help coordinate and channel the energy?
• State gov seems incredibly nimble here – seconding people from departments all over to the crisis, etc.  Bureaucracy is real, but it can melt away in an emergency, or when the governor wants it to. Really impressive
• Going to try DoorDash and see if it’s any different than UberEats.  (It’s not.) Big night.

Saturday, March 21, Day 5

• Saturday but office still 75%
• Wellness Screening again.  Still can’t get thermometer to work for quite a while
• Mike Willis asked for feedback and observations (good) – they are
  • Atmosphere in EOC calm, focused, integrated, SMART, nimble, fast – opposite of “government”
  • Opening meeting on Tuesday morning – calm, focused, caring, quiet urgency
  • Didn’t realize he was military
  • Mentioned yesterday’s “not vetted, not integrated, not helpful” moment, poignant but respectful
• Team pull up, drowning in emails, plan to get organized
• Governor briefing
• Working on replacing me…
• Seamless prioritization of things that are gateway items and enablers.  We have a project tracker, but it’s almost useless. Mostly we are just doing prioritization in the moment.  No choice. Crisis mode
• Gov call – carefully weighing isolation strategy (economic as well as risk of civil disobedience) with number of projected deaths – sounds like the same conversation I’m reading about in the papers at the national level, but really interesting to see it up close and personal. Asked for plan around making food and services safer – super thoughtful “it’s not the economic activity that causes problems, it’s social proximity, are there ways we can keep one and minimize the other?”
• Colorado still has around 500 cases statewide – about ¼ of Westchester County.  Denver has less than 100. Still, feels like we are watching the tsunami coming at us in slow motion
• Dinner at a very close friend’s house who lives in town – elbow bumps and sat at the other end of the table.  Fun and social, but feels like even things like this are about to come to an end. Got to do laundry

Sunday, March 22, Day 6

• Sunday but office still 75%
• Multiple failures again with wellness screen, then we figure it out – on the walk over from the hotel, it’s cold enough that my skin temperature is out of range for the contact thermometers they have.  Since I am coming in early when there is no line, my face is too cold when I get to the front
• Adding staff, nowhere to put them, no organized email lists, working on org charts, have to retool O/S for meetings/tasks.  A little chaotic, but at least I know how to do this stuff
• Finally got connection to NY State to do some benchmarking on testing – doesn’t seem like states coordinate or share info a lot, but the team there was happy to 
• Finally have a few minutes to do planning on major swim lanes
• More working on replacing me
• This is the problem with statistics.  Models are only as good as the inputs, and the inputs here seem like they’re all over the place…not just here in CO, but everywhere.  It’s not like we have a pandemic every year to refine our math
• Interviewing Sarah Tuneberg (came in via Brad) to replace me with Lisa and Stan – she’s AWESOME and she’s hired – starts on the spot by coming in to stand with us behind the Governor at a press conference.  Talk about a rapid recruiting process!
• Seems like she will be awesome.  Probably way better than me – has a ton of public health and emergency/disaster response experience in addition to some private sector/startup/tech experience
• Her first worry never even occurred to me – Fatality Management – morgue surge capacity.  “Gift to the living” – so awesome
• Lameness of Trump press conference – self praise followed by sycophants in the midst of a typhoon
• Gov press conference (here) – authentic and well received.  “Grim reaper” was quite poignant. He worked in the key messages we asked him to about public misinformation of testing, talking points was Google Doc with 30+ people in it – good example of collaboration and control, seamless, last minute but still came out great.  Announces social distancing and lots of good examples about groceries, jogging, still no lockdown
• Lots of RP Colorado people seeing press conference…phone buzzing like mad in my pocket!  So many awesome notes from friends and former colleagues thanking me for being there to help, only one or two snarky comments about my orange tee shirt while others were in blazers (hey, it was a Sunday and the presser was called last minute!)

Stay tuned for more tomorrow…

I have an end of year work routine that’s a pull-up and self-assessment. I’ve been doing this for years, and I’ve written about its evolution in Part I and Part II of this series.

I’ve always taken a few minutes at this time of the year to ask myself these four questions:

• Am I having fun at work?
• Am I learning and growing as a professional?
• Is my work financially rewarding enough, either in the short-term or in the long-term?
• Am I having the impact I want to have on the world?

If I answer at least 2.5 of these questions as yes, I feel like things are on track. If I am below that, or even at 2.5 sometimes, it’s time for a rethink of what I’m doing or how I’m doing it.

I was having lunch with my friend Bryton, the CEO of Aquabyte, a few weeks back, and that conversation spurred on a 5th question, which I’ll now add to my end of year routine:

• Am I excited about what I’m doing?

I’ve realized now that I’m over two years into the journey at Bolster that there’s a significant value in being really into the subject matter of the business. I thought I was at Return Path…but now I realize that I wasn’t nearly as excited about what I was doing as I could have been. Our work at Bolster of helping founders be more successful is more personally meaningful to me than solving email deliverability challenges. That work had real impact on the world…but I just wasn’t into it as much.

And that makes a big difference in answering the general question of “Am I on track?” at the end of the year. I’ll skip next week and see you all in 2023. Happy New Year and Happy Holidays, everyone!

I’ve written a couple times this past year about our ReturnShip program, which is a 4-month paid internship program designed for women who have been out of the workforce for more than 3 year to re-enter and  build credible and relevant experience, and to expand the talent pool for our organization.  I wrote about the initial concept when we launched v2 of the program, and then again when v2 concluded with the hiring of four of the six participants.

I’m immensely proud of our organization for inventing the program (Andy Sautins, our CTO, gets credit) and for managing it so well during the last cycle (Cathy Hawley, our VP People, and Miranda Reeves, VP Solution Management, get lead credit, but lots of other people had a hand in its success).

Yesterday, we officially launched v3 of the program and are very excited about how it is scaling.  The launch was coincident with a visit to our office by Congressman Jared Polis, who represents our district in Colorado, as part of his Startup Day Across America visit to the district, which was exciting for us.

v3 of the program is poised to take the concept to the next level.  We will have almost 40 Returnees in the program – but we’ve taken the program beyond Return Path and beyond our Colorado office.  We are going to place Returnees in five locations – Broomfield, Colorado, New York City, Austin, Indianapolis, and London – and we recruited five like-minded partner companies to join the program as well.  SendGrid, ReadyTalk, MWH Global, and SpotXchange will participate in the program in the Denver area, and Seattle-based Moz will participate as well.  We are still going to administer the program out of Return Path, with Andy and Cathy being joined by Katie Green from our People team as well as Laura Harrison, one of our v2 Returnees, as program manager (among others).

We are starting the recruiting cycle now for the program, which starts mid-October.  While we are getting a centralized web site up and running, in the meantime, you can see the available openings on the respective company web sites:

• ReturnPath @ http://bit.ly/1PhaweF
• MWH Global @ http://bit.ly/1JfHUgz
• SpotXchange @ http://bit.ly/1CPqR22
• Sendgrid  @ http://bit.ly/1CTmjtk
• ReadyTalk @ http://bit.ly/1gu4sU1
• Moz (coming soon)

Here are a couple pictures from our time with Congressman Polis yesterday – one of him and Laura Harrison, Karen Brockwell, and Lisa Stephens (three of our v2 Returnees), and one of me along with representatives of the other participating companies.

Book Short:  On The Same Page

Being on the same page with your team, or your whole company for that matter, is a key to success in business.  The Four Obsessions of an Extraordinary Executive, by Patrick Lencioni, espouses this notion and boils down the role of the CEO to four points:

1. Build and maintain a cohesive leadership team
2. Create organizational clarity
3. Overcommunicate organizational clarity
4. Reinforce organizational clarity through human systems

Those four points sound as boring as bread, but the book is anything but.  The book’s style is easy and breezy — business fiction.  One of the most poignant moments for me was when the book’s “other CEO” (the one that doesn’t “get it”) reflects that he “didn’t go into business to referee executive team meetings and delivery employee orientation…he loved strategy and competition.”  Being a CEO is a dynamic job that changes tremendously as the organization grows.  This book is a great handbook for anyone transitioning out of the startup phase, or for anyone managing a larger organization.

I haven’t read the author’s other books (this is one in a series), but I will soon!

The Best Place to Work, Part 4: Be the Consummate Host

Besides Surrounding yourself with the best and brightest , Creating an environment of trust,  and Managing yourself very, very well, it’s important for you as a creator of The Best Place to Work to Be the Consummate Host.

What does that mean?  This is how I approach my job every day.  I think of the company as a party, where I’m the host.  I want everyone to have a good time.  To get along with the other guests.  To be excited to come back the next time I have a party (e.g., every day).

By the way, I always have co-hosts, as well – anyone who manages anyone in the company.  If I can’t do something specific below, someone on my executive team does it.  Sometimes, two of us do it!  Examples include:

• I interview people like I’m a bouncer at an exclusive club.  We do very personal new employee orientations.  We do personal check-ins after 30 and 90 days to make sure new employees are on track
• I attend every company function that I can and work the room as a host, even if it’s not “my” event – sometimes it means sacrificing long conversations and conversations with friends for smaller ones and meeting new people
• I call every employee (voicemail ok) and write a note and/or send a gift every anniversary of their employment with the company
• I write notes to people when they do something great or get a promotion

Full series of posts here.

Part of creating the best place to work  is learning how to self manage – very, very well.  This is an essential part of Creating an environment of trust , but only one part.  What does self-management mean?  First, and most important, it means realizing that you are in a fishbowl.  You are always on display.  You are a role model in everything you do, from how you dress, to how you talk on the phone, to the way you treat others, to when you show up to work. 

But what are some specifics to think about while you swim around in your tank?

1. Don’t send mixed signals to the team.  You can’t tell people to do one thing, then do something different yourself
2. Remember the French Fry Theory of being a CEO.  My friend Seth has the French Fry theory of life, which is simply that you can always eat one more French fry.  You’re never too full for one more fry.  You might not order another plate of them, but one more?  No problem.  Ever.  As a CEO, you can always do one more thing.  Send one more email.  Read one more document.  Sometimes you just need to draw the line and go home and stop working!  (See my earlier post  here  on how Marketing is like French Fries for another example.)
3. Regularly solicit feedback, then internalize it and act on it.  Do reviews for the company.  Do anonymous 360s (I’ve written about these regularly here). Get people a review that has ratings and comments from their boss, their peers, and their staff.  Do them once a year at a minimum.  And do one for yourself.  They’re phenomenal.  Everyone needs to improve, always.  Our head of sales Anita always says “Feedback is a gift, whether you want it or not.”  Make sure you do them for yourself as well.  Include your Board.  If you don’t agree with the feedback you are being given that is likely a data point that you have a BLIND SPOT.  Being defensive about feedback is dangerous.  If you don’t get it/don’t like then do some more work to better understand it.  Otherwise you will forever be defensive and never develop in this area
4. Maintain your sense of humor.  It’s not only the best medicine, it’s the best way to stay sane and have fun.  Who doesn’t want to have fun at work?
5. Keep yourself fresh:  Join a CEO peer group.  Work with an executive coach.  Read business literature (blogs, books, magazines) like mad and apply your learnings.  Exercise regularly.  Don’t neglect your family or your hobbies.  Keep the bulk of your weekends, and at least one two-week vacation each year, sacrosanct and unplugged.  As Covey would say, Sharpen the Saw

You set the tone at your company.  You can’t let people see you sweat too much – especially as you get bigger.  You can’t come out of your office after bad news and say “we’re dead!”  You can make a huge difference by being a great role model, swimming around in your fishbowl.

Automated Love

Return Path is launching a new mini feature sometime this week to our clients.  Normally I wouldn’t blog about this — I think this is mini enough that we’re probably not even saying much about it publicly at the company.  But it’s an interesting concept that I thought I’d riff on a little bit.

I forget what we’re calling the program officially — probably something like “Client Status Emails” or “Performance Summary Alerts” — but a bunch of us have been calling it by the more colorful term “Automated Love” for a while now.

The art of account management or client services for an on-demand software company is complex and has evolved significantly from the old days of relationship management.  Great account management now means a whole slew of new things, like Being The Subject Matter Expert, and Training the Client.  It’s less about the “hey, how are things going?” phone call and more about driving usage and value for clients.

As web services have taken off, particularly for small businesses or “prosumers,” most have built in this concept of Automated Love.  The weekly email from the service to its user with charts, stats, benchmarks, and links to the web site, occasionally with some content or blog posts.  It’s relatively easy (most of the content is database driven), it reminds customers that you’re there, working on their behalf in the background, it tells them what happened on their account or how they’re doing, it alerts them to current or looming problems, and it drives usage of your service.  As a bonus for you internally, usually the same database queries that produce a good bit of Automated Love can also alert your account management team when a client’s usage pattern of your service changes or stops entirely.

While some businesses with low values of any single customer value can probably get away with having a client service function based ENTIRELY on Automated Love, I think any business with a web service MUST have Automated Love as a component of its client service effort.

First in my series of posts around creating the best place to work  is to Surround yourself with the best and brightest.  This one is simple.  Build the best team you can possibly build…as you need it.

As a founder, you may be the best person at doing everything in your company, especially if you are a technical founder.  But as my long-time Board member at Return Path Greg Sands always says, when the organism grows, cells start to specialize.  Eventually, you need a liver and a brain.  Just like companies need a head of sales and a CFO (not to imply that Anita likes the occasional cocktail or that Jack likes math – turns out both like both).

How does this come into play as a CEO?

-Don’t be afraid to hire people better than you at their specialty – older, wiser, more experienced, more expensive

– Check references carefully – don’t get suckered in by resume or rolodex – some successful big company people don’t actually know how to do work or build a business, so you have to dig and find back-channel references

– Don’t overhire before you’re ready, but especially as a start-up, better to hire 3 months before you need the position, not 6 months too late

-Remember that you are the CEO.  Even if you hire very experienced people in specific roles, you have the best global view of everything going on in the company.  And you need to pay attention to people on your team and actively manage them, even experts who are older or wiser than you are

Surrounding yourself with the best and brightest can be daunting and even threatening to some CEOs.  But you have to do it to grow your business.  And you have to keep doing it as you keep growing your business (and your staff has to do the same!).

5 Ways to Get Your Staff on the Same Page

[This post first appeared as an article in Entrepreneur Magazine as part of a new series I’m publishing there in conjunction with my book, Startup CEO:  A Field Guide to Scaling Up Your Business]

When a major issue arises, is everybody at your company serving the same interests? Or is one person serving the engineering team, another person serving the sales team, one board member serving the VC fund, another serving the early-stage “angels” and another serving the CEO? If that’s the case, then your team is misaligned. No individual department’s interests are as important as the company’s.

To align everyone behind your company’s interests, you must first define and communicate those goals and needs. This requires five steps:

1. Define the mission. Be clear to everyone about where you’re going and how you’re going to get there (in keeping with your values).
2. Set annual priorities, goals, and targets. Turn the broader mission into something more concrete with prioritized goals and unambiguous success metrics.
3. Encourage bottom-up planning. You and your executive team need to set the major strategic goals for the company, but team members should design their own path to contribution. Just be sure that you or their managers check in with them to assure that they remain in synch with the company’s goals.
4. Facilitate the transparent flow of information and rigorous debate. To help people calibrate the success, or insufficiency, of their efforts, be transparent about how the organization is doing along the way. Your organization will make better decisions when everyone has what they need to have frank conversations and then make well-informed decisions.
5. Ensure that compensation supports alignment (or at least doesn’t fight it). As selfless as you want your employees to be, they’ll always prioritize their interests over the company’s. If those interests are aligned – especially when it comes to compensation – this reality of human nature simply won’t be a problem.

Taken in sequence, these steps are the formula for alignment. But if I had to single out one as the most important, it would be number 5: aligning individual incentives with companywide goals.

It’s always great to hear people say that they’d do their jobs even if they weren’t paid to, but the reality of post-lottery-jackpot job retention rates suggests otherwise. You, and every member of your team, “work” for pay. Whatever the details of your compensation plan, it’s crucial that it aligns your entire team behind the company’s best interests.

Don’t reward marketers for hitting marketing milestones while rewarding engineers to hit product milestones and back office personnel to keep the infrastructure humming. Reward everybody when the company hits its milestones.

The results of this system can be extraordinary:

• Department goals are in alignment with overall company goals. “Hitting product goals” shouldn’t matter unless those goals serve the overall health of your company. When every member of your executive team – including your CTO – is rewarded for the latter, it’s much easier to set goals as a company. There are no competing priorities: the only priority is serving the annual goals.
• Individual success metrics are in alignment with overall company success metrics. The one place where all companies probably have alignment between corporate and departmental goals is in sales. The success metrics that your sales team uses can’t be that far off from your overall goals for the company. With a unified incentive plan, you can bring every department into the same degree of alignment. Imagine your general counsel asking for less extraneous legal review in order to cut costs
• Resource allocation serves the company, rather than individual silos. If a department with its own compensation plan hits its (unique) metrics early, members of that team have no incentive to pitch in elsewhere; their bonuses are secure. But if everyone’s incentive depends on the entire company’s performance, get ready to watch product leads offering to share developers, unprompted.

This approach can only be taken so far: I can’t imagine an incentive system that doesn’t reward salespeople for individual performance. And while everyone benefits when things go well, if your company misses its goals, nobody should have occasion to celebrate. Everybody gets dinged if the company doesn’t meet its goals, no matter how well they or their departments performed. It’s a tough pill to swallow, but it also important preventive medicine.

Scaling the Team

(This post was requested by my long-time Board member Fred Wilson and is also running concurrently on his blog today.  I’ll be back with the third and fourth installments of “The Best Laid Plans” next Thursday and the following Thursday)

When Return Path reached 100 employees a few years back, I had a dinner with my Board one night at which they basically told me, “Management teams never scale intact as you grow the business.  Someone always breaks.”  I’m sure they were right based on their own experience; I, of course, took this as a challenge.  And ever since then, my senior management team and I have become obsessed with scaling ourselves as managers.  So far, so good.  We are over 300 employees now and rapidly headed to 400 in the coming year, and the core senior management team is still in place and doing well.  Below are five reasons why that’s the case.

1. We appreciate the criticality of excellent management and recognize that it is a completely different skill set from everything else we have learned in our careers.  This is like Step 1 in a typical “12-step program.”  First, admit you have a problem.  If you put together (a) management is important, (b) management is a different skill set, and (c) you might not be great at it, with the standard (d) you are an overachiever who likes to excel in everything, then you are setting the stage for yourself to learn and work hard at improving at management as a practice, which is the next item on the list.
2. We consistently work at improving our management skills.  We have a strong culture of 360 feedback, development plans, coaching, and post mortems on major incidents, both as individuals and as a senior team.  Most of us have engaged on and off over the years with an executive coach, for the most part Marc Maltz from Triad Consulting.  In fact, the team holds each other accountable for individual performance against our development plans at our quarterly offsites.  But learning on the inside is only part of the process.
3. We learn from the successes and failures of others whenever possible.  My team regularly engages as individuals in rigorous external benchmarking to understand how peers at other companies – preferably ones either like us or larger – operate.  We methodically pick benchmarking candidates.  We ask for their time and get on their calendars.  We share knowledge and best practices back with them.  We pay this forward to smaller companies when they ask us for help.  And we incorporate the relevant learnings back into our own day to day work.
4. We build the strongest possible second-level management bench we can to make sure we have a broad base of leadership and management in the company that complements our own skills.  A while back I wrote about the Peter Principle, Applied to Management that it’s quite easy to accumulate mediocre managers over the years because you feel like you have to promote your top performers into roles that are viewed as higher profile, are probably higher comp – and for which they may be completely unprepared and unsuited.  Angela Baldonero, my SVP People, and I have done a lot here to ensure that we are preparing people for management and leadership roles, and pushing them as much as we push ourselves.  We have developed and executed comprehensive Management Training and Leadership Development programs in conjunction with Mark Frein at Refinery Leadership Partners.  Make no mistake about it – this is a huge investment of time and money.  But it’s well worth it.  Training someone who knows your business well and knows his job well how to be a great manager is worth 100x the expense of the training relative to having an employee blow up and needing to replace them from the outside.
5. We are hawkish about hiring in from the outside.  Sometimes you have to bolster your team, or your second-level team.  Expanding companies require more executives and managers, even if everyone on the team is scaling well.  But there are significant perils with hiring in from the outside, which I’ve written about twice with the same metaphor (sometimes I forget what I have posted in the past) – Like an Organ Transplant and Rejected by the Body.  You get the idea.  Your culture is important.  Your people are important.  New managers at any level instantly become stewards of both.  If they are failing as managers, then they need to leave.  Now.

I’m sure there are other things we do to scale ourselves as a management team – and more than that, I’m sure there are many things we could and should be doing but aren’t.  But so far, these things have been the mainstays of happily (they would agree) proving our Board wrong and remaining intact as a team as the business grows.