(This is the fifth post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, 3, and 4.)

Thursday, March 26, Day 10

• Sarah continuing to take over and stronger by the day
• Sarah cleared me to go home, only one more person to ask
• Deep deep dive on Mass Testing – so good to spend that time 
• Pretty much got the strategy right – shocking we could get that close with so little public health experience – Kyle awesome – EOC leadership briefing
• That was most of the day
• Some downloads to Sarah and Kacey
• Feeling that two of our project teams are going sideways – that will be a big focus for me tomorrow before I leave
• Quick assignments for tomorrow
• Talked to Jared – he’s good with me going now that Sarah is in place and things are running.  Awesome!

Friday, March 27,  Day 11

• Download with a couple of the project teams to help get them back on track 
• This whole thing is one big exercise in Agile!
• Serendipitously might have found private sector partner for one of the teams in need.  Reminded of George’s great line, “when the student is ready, the teacher appears”
• Gov briefing on mass testing plan
• Spent a lot of the day on strategy/overview/retrospective deck.  Have to review it with Brad and core team members. Gov wants to get it in front of the National Governors Association to share learnings/best practices for the states behind us in this fight
• Gov thankful goodbye
• Brad thank you Haiku – so awesome – “You see things others don’t see”
• FInal team check-in, lots of nice thank yous from people on team
• Close out drinks with Sarah, Kacey, Kyle – persevered despite lack of corkscrew.  Poor Kyle’s shirt looks like he was standing next to a shooting victim
• Incredibly thankful moment with team – really like and care about these people – we’ve done such great work together – 11 days but feels like months and months
• Close out email to Governor and Chief of Staff about team

Saturday, March 28, Day 12

• Check out!  Fly home! Happy to see Mariquita, Casey, Wilson, and Elyse!

Stay tuned for two more wrap-up posts, tomorrow and the next day…

Back to…

I’m not in school any more, and as far as I can tell now, schools start before Labor Day for the most part, but it still feels like tomorrow is “back to school” for the working world. Business still hums along in August, and we’ve certainly had our hands full with one of the busiest months ever at Return Path, but somehow, the traditional end of the summer season still manages to have the trappings of a European August, with lots of people on vacation or doing more “work from home” days than usual.

As all that draws to a close today, at least for me personally, it’s Back to…lots of things:

– Back to New York! After a few weeks out of the city at our house in the mountains, it’s great to be back in Metropolis

– Back to shorter and more varied workouts! Training for my recent half marathon meant a lot of long runs and not much else. Now back to weights, pilates, elliptical, and swimming

– Back to more serious reading! I’ve read a bunch of trash over the summer. I was way overdue. My brain was starting to hurt. So I tuned out of almost all news, business books, and non-fiction for a month, and I plowed through enough murder mysteries to wallpaper a library (no doubt one populated by Colonel Mustard and Mrs. Peacock)

– Back to business! A few days and half days off and some working from home behind me, it’s time to gear up for a very busy September and October. Always busy months with industry events and pre-holiday retail client frenzy, this year will be even busier as we work to integrate our recent acquisition of Habeas as well as complete a number of other big initiatives

So happy Labor Day, which Wikipedia notes was created in 1882 and federalized in 1894 as “a day off for its working citizens.”

I was honored this week to be in a small group “fireside chat” with Angela Duckworth, author of the book Grit: The Power of Passion and Perseverance, and to meet her and ask a question.

I want to hit on one theme here from the book and dialog, but I’ll start by sharing a 2×2 matrix (remember, I’m an ex-consultant, I think in frameworks) that we’ve used at home with our kids periodically. For the most part, we use it to talk to them about why they should work harder on math homework, but it’s had other use cases as well. Hopefully it makes sense on the face of it…

…but essentially the framework teaches that if you are talented AND work hard at something, you can achieve great things. If you have talent and slack off, you can get by perfectly fine. If you have no talent but work your butt off, you can get there…but it’s hard. And if there’s an area of life where you have no talent and don’t work at it, so be it, but you’re punting on that whole thing.

In the book, Duckworth takes this to a whole new level by adding a simultaneous second equation:

• Talent x Effort = Skill
• Skill x Effort = Achievement

This makes the statement that “your first bit of talent, combined with effort increases your skill level. Your increasing skill, multiplied by effort, leads to achievement. That means effort counts twice. Once for skill and once for achievement. But that doesn’t mean it’s twice as important. If you substitute the skill equation into the achievement equation, you end up with

• Talent x Effort x Effort = Achievement, which means that 
• Talent x Effort² = Achievement.

Or in other words, “Your effort is exponentially more important than how talented you are.”

All I have to say is that while I won’t create a second graphical explanation of this and probably won’t go back and amend my 2×2 for my kids, I think Duckworth is right, with one caveat. If you don’t have a certain baseline of talent in a certain area, it just doesn’t matter how much effort you apply – your achievement has some kind of natural governor to it. When I was a kid, I would dearly have loved to be the shortstop for the San Diego Padres, but between being a lefty, a kid, and not what you would call overly athletic, it wouldn’t have mattered if I spent every waking hour of a decade working at it…I never would have gotten there. Having said that, those cases may be edge cases, and again, I find that the emphasis on effort on top of my framework is a very worth application.

But go read Grit. It’s much better and more detailed than this blog post!

Good Meeting Behavior

I've been in meetings with large groups of people at big companies where they're all on laptops the whole meeting, no one makes any eye contact with the speaker/facilitator, and it's hard to get a pulse out of the group as a result.

I almost entirely stopped bringing laptops and smartphones into business meetings a few years back.  There's nothing I find more irritating than when other people are using them when it's my meeting.  Even if they're taking notes, I never know if they're really taking notes or sneaking a peek at email.  And in my experience, people who are on laptops and phones in meetings, whatever they're doing on those devices and however good they are at multi-tasking, aren't paying as close attention to the meeting as the other people in the room. 

What I do instead is take notes on paper and spend 2 minutes after the meeting handling whatever data entry I need to handle on my computer.

I was very excited to see Brad's post about how he is now going to take paper notes in Board meetings rather than use his smartphone and be tempted to check email (and otherwise be distracted).  Everyone should do this for every meeting.  Board meetings are important examples, but they're not alone.  It's just good meeting behavior.  If you have other things to do, step out of the meeting and do them.

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…

The Gift of Insight

Jonathan Schwartz has a great post entitled “Every Customer Visit is a Lesson.” It’s so true…if you want to give yourself a gift this holiday season, give yourself the gift of insight and spend some time in the market with a few of your top customers or prospects.  I’ve always found that to be one of the most valuable ways to shape the business, both strategically and operationally.

One of the most vivid memories I have to illustrate this concept is a meeting that I had with Crate and Barrel, a prospect, in the very early days of Return Path, back in 2000 or 2001.  I went in with my colleague Sophie Miller, and with a number of product sales specialists from our reseller, DoubleClick, for an all-day session with C&B’s online marketing team.  We collectively were pitching everything, possibly including the kitchen sink — ad serving through DART, buying online media through the DoubleClick Network, using Abacus to expand the reach of their catalog, sending email through DARTMail, renting email lists through DoubleClick’s email list business, oh yes, and using Return Path’s ECOA service to keep their email database clean.

The meeting was a mess, and as far as I can tell, it didn’t really lead to any meaningful business, either for us or for DoubleClick.  I learned two things in this call the hard way, but both were incredibly valuable lessons that continue to shape our business today.

First, we created massive confusion by bringing multiple sales people in to each present a specific product to the customer, rather than sending in one senior, consultative sales person to present a holistic digital marketing solution.  Picture yourself as the head of e-commerce for a major retailer, expecting an insightful day with the leading vendor in the space…then walking into the meeting and seeing that vendor’s SEVEN different sales people introducing themselves to each other!  It was a mess.  Since then, we have tried hard (and I think DoubleClick has as well) to run with a single sales force organized around the customer, not organized around our own products.

Second, we discovered that the original version of our flagship ECOA product (which was still in beta at the time) had a couple of flaws in the business model that were probably going to make it a non-starter in the retail/catalog vertical.  We also learned, happily, that the client loved the concept, but there were some details in the original product that had to be fixed if we were ever going to get traction with key customers in that key segment.  We fixed these problems and were able to successfully re-launch ECOA later that year, but more important, we now stay much closer to our customers as we develop new products and features so we make sure concepts are more firmly market tested before they head into development.

There are many more examples of this Gift of Insight, which I’ll share in future posts.  Happy Holidays!

As I mentioned in a previous post, I write a column for The Magill Report, the new venture by Ken Magill, previously of Direct magazine and even more previously DMNews. I share the column with my colleagues Jack Sinclair and George Bilbrey and we cover how to approach the business of email marketing, thoughts on the future of email and other digital technologies, and more general articles on company-building in the online industry – all from the perspective of an entrepreneur. I recently posted George’s column on Staying Innovative as Your Business Grows (Part One). Below is a re-post of George’s second part of that column from this week, which I think my OnlyOnce readers will enjoy.

Guest Post: Staying Innovative as Your Business Grows (Part Two)

By George Bilbrey
Last month, as part of the Online Entrepreneur column, I shared some of Return Path’s organizational techniques we use to stay innovative as we grow. In this article, I’ll talk about the process we’re using in our product management-and-development teams to stay innovative.

The Innovation Process at Return Path
As we grew bigger, we decided to formalize our process for bringing new products to market. In our early days we brought a lot of new products to market with less formal process but also with more limited resources. We did well innovating one product at a time without that kind of process largely because we had a group of experienced team members. As the team grew, we knew we had to be more systematic about how we innovated to get less experienced product managers and developers up to speed and having an impact quickly.

We had a few key objectives when designing the process:

• We wanted to fail fast – We had a lot of new product ideas that seemed like good ones. We wanted a process that allowed us to quickly determine which ideas were actually good.

• We wanted to get substantial customer feedback into the process early – We’d always involved clients in new product decisions, but generally only at the “concept” phase. So we’d ask something like “Would you like it if we could do this thing for you?” which often elicited a “Sure, sounds cool.” And then we’d go off and build it. We wanted a process that instead would let us get feedback on features, function, service levels and pricing as we were going so we could modify and adjust what we were building based on that iterative feedback.

• We wanted to make sure we could sell what we could build before we spent a lot of time building it – We’d had a few “build it and they will come” projects in the past where the customers didn’t come. This is where the ongoing feedback was crucial.

The Process
We stole a lot of our process from some of the leading thinkers in the “Lean Startup” space – particularly Gary Blanks’ Four Steps to the Epiphany and Randy Komisar’s Getting to Plan B. The still-evolving process we developed has four stages:

Stage 1: Confirm Need

Key Elements

• Understand economic value and size of problem through intense client Interaction
• Briefly define the size of opportunity and rough feasibility estimate – maybe with basic mockups
• Key Question: Is the need valid? If yes, go on. If no, abandon project or re-work the value proposition.

Stage 2: Develop Concept

Key Elements

• Create a high fidelity prototype of product and have clients review both concept and pricing model
• Where applicable, use data analysis to test feasibility of product concept
• Draft a more detailed estimate of effort and attractiveness, basically a business model
• Key Question: Is the concept Valid? If yes, go on. If no, abandon project.

Stage 3: Pilot

Key Elements

• Build “minimum viable product” and sell (or free beta test with agreed to post beta price) with intense client interaction and feedback
• Develop a marketing and sales approach
• Develop a support approach
• Update the business model with incremental investment requirements
• Preparation of data for case studies
• Key Question: Is project feasible? If yes, go on. If no, abandon project or go back to an earlier stage and re-work the concept.

Stage 4: Full Development and Launch

Key Elements

• Take client feedback from Pilot and apply to General Availability product
• Create support tools required
• Create sales collateral, white papers, lead generation programs, case studies and PR plan.
• Train internal teams to sell and service.
• Update business model with incremental investment required
• Go forth and prosper

There are a several things to note about this process that we’ve found to be particularly useful:

• A high fidelity prototype is the key to getting great customer feedback – You get more quality feedback when you show them something that looks like the envisioned end product than talking to them about the concept. Our prototypes are not functional (they don’t pull from the databases that sit behind them) but are very realistic HTML mockups of most products.

• Selling the minimum viable product (MVP) is where the rubber meets the road – We have learned the most about salability and support requirements of new products by building an MVP product and trying to sell it.

• Test “What must be true?” during the “Develop Concept” and “Pilot Phases” – When you start developing a new product, you need to know the high risk things that must be true (e.g., if you’re planning to sell through a channel, the channel must be willing and able to sell). We make a list of those things that must be true and track those in weekly team meetings.

• This is a very cross functional process and should have a dedicated team – This kind of work cannot be done off the side of your desk. The team needs to be focused just on the new product.

While not without bumps, our team has found this process very successful in allowing us to stay nimble even as we become a much larger organization. As I mentioned in Part 1, our goal is really to leverage the strengths of a big company while not losing the many advantages of smaller, more flexible organizations.

What Makes an Awesome Board Member

(This post was requested by my long-time Board member Brad Feld and is also running concurrently on his blog today)

I’ve written a bunch of posts over the years about how I manage my Board at Return Path.  And I think part of having awesome Board members is managing them well – giving transparent information, well organized, with enough lead time before a meeting; running great and engaging meetings; mixing social time with business time; and being a Board member yourself at some other organization so you see the other side of the equation.  All those topics are covered in more detail in the following posts:  Why I Love My Board, Part II, The Good, The Board, and The Ugly, and Powerpointless.

But by far the best way to make sure you have an awesome board is to start by having awesome Board members.  I’ve had about 15 Board members over the years, some far better than others.  Here are my top 5 things that make an awesome Board member, and my interview/vetting process for Board members.

Top 5 things that make an awesome Board member:

• They are prepared and keep commitments.  They show up to all meetings.  They show up on time and don’t leave early.  They do their homework.  The are fully present and don’t do email during meetings
• They speak their minds.  They have no fear of bringing up an uncomfortable topic during a meeting, even if it impacts someone in the room.  They do not come up to you after a meeting and tell you what they really think.  I had a Board member once tell my entire management team that he thought I needed to be better at firing executives more quickly!
• They build independent relationships.  They get to know each other and see each other outside of your meetings.  They get to know inviduals on your management team and talk to them on occasion as well.  None of this communication goes through you
• They are resource rich.  I’ve had some directors who are one-trick or two-trick ponies with their advice.  After their third or fourth meeting, they have nothing new to add.  Board members should be able to pull from years of experience and adapt that experience to your situations on a flexible and dynamic basis
• They are strategically engaged but operationally distant.   This may vary by stage of company and the needs of your own team, but I find that even Board members who are talented operators have a hard time parachuting into any given situation and being super useful.  Getting their operational help requires a lot of regular engagement on a specific issue or area.  But they must be strategically engaged and understand the fundamental dynamics and drivers of your business – economics, competition, ecosystem, and the like

My interview/vetting process for Board members:

• Take the process as seriously as you take building your executive team – both in terms of your time and in terms of how you think about the overall composition of the Board, not just a given Board member
• Source broadly, get a lot of referrals from disparate sources, reach high
• Interview many people, always face to face and usually multiple times for finalists.  Also for finalists, have a few other Board members conduct interviews as well
• Check references thoroughly and across a few different vectors
• Have a finalist or two attend a Board meeting so you and they can examine the fit firsthand.  Give the prospective Board member extra time to read materials and offer your time to answer questions before the meeting.  You’ll get a good first-hand sense of a lot of the above Top 5 items this way
• Have no fear of rejecting them.  Even if you like them.  Even if they are a stretch and someone you consider to be a business hero or mentor.  Even after you’ve already put them on the Board (and yes, even if they’re a VC).  This is your inner circle, and getting this group right is one of the most important things you can do for your company

I asked my exec team for their own take on what makes an awesome Board member.  Here are some quick snippets from them where they didn’t overlap with mine (with only two inside jokes that I couldn’t resist putting up for the Board):

• Ethical and high integrity in their own jobs and lives
• Comes with an opinion
• Thinking about what will happen next in the business and getting management to think ahead
• Call out your blind spots
• Remembering to thank you and calling out what’s right
• Role modeling for your expectations of your own management team – Do your prep, show up, be fully engaged, be brilliant/transparent/critical/constructive and creative.  Then get out of our way
• Offer tough love…Unfettered, constructive guidance – not just what we want to hear
• Pattern matching:  they have an ability to map a situation we have to a problem/solution at other companies that they’ve been involved in – we learn from their experience…but ability and willingness to do more than just pattern matching.  To really get into the essence of the issues and help give strategic guidance and suggestions
• Ability to down 2 Shake Shack milkshakes in one sitting
• Colorful and unique metaphors

Disclaimer – I run a private company.  While I’m sure a lot of these things are true for other types of organizations (public companies, non-profits, associations, etc.), the answers may vary.  And even within the realm of private companies, you need to have a Board that fits your style as a CEO and your company’s culture.  That said, the formula above has worked well for me, and if nothing else, is somewhat time tested at this point!

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

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

Every CEO faces dilemmas like this all the time.

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

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

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

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

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

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

How to Ask For a Raise

I’m guessing this topic will get some good play, both internally at Return Path and externally.  It’s an important topic for many reasons, although one of the best ones I can think of is that most people aren’t comfortable asking for raises (especially women and more introverted people, according to lots of research as well as Sheryl Sandberg’s Lean In).

My whole point in writing this is to make compensation part of normal conversations between a manager and a team member.  This requires the manager making it comfortable (without negative stigma), and the employee approaching it maturely.

My guess is that the two most common ways most people ask for raises when they bother to do so are (1) they get another job offer and try to get their current employer to match, or (2) they come to their boss with a very emotional appeal about how hard they are working, or that they heard Sally down the hall makes more money than they do, and that’s not fair.  Although either one may work (particularly the first one), there’s a better way to think about the whole process that removes the emotion and produces a better outcome for both employer and company.

Compensation is fundamentally a data-driven process for companies.  The high-level data inputs are the size of payroll, the amount of aggregate increase the company can afford, and the framework for distributing that aggregate increase by department or by level of performance.  A second set of position- or person-specific data looks at performance within a level, promotions, and internal leveling, and external comparables.  Fundamentally, smart companies will approach compensation by paying people fairly (both internally and externally) to do their jobs so they keep their best people from looking for new jobs because of compensation.

If compensation is a data-driven process for companies, employees should treat asking for raises as a data-driven process, too.  How can you go about that?  What data can you bring to a compensation conversation with your manager to make it go as smoothly as possible?

1. Let your manager know ahead of time that you’d like to discuss your compensation at your next 1:1, so he or she is prepared for that topic to come up.Blindsiding will never result in a calm and collected conversation.
2. Be mindful of the company’s compensation cycle timing.  If the company has an annual process and you are just about to hit it (within 2-3 months), then consider carefully whether you want to ask for a raise off-cycle, or whether you just want to give your manager data to consider for the company’s normal cycle.  If you’re really off-cycle (e.g., 4-8 months away), then you should note to your manager that you’re specifically asking for off-cycle consideration
3. Bring internal data:  your most recent performance review or ratings as well as any other specific feedback or praise you’ve received from your manager, colleagues, or senior people.  See below for one additional thought on internal data
4. Bring external data:  bring in compensation and job requirement and scope data from multiple online sources, or even from recruiters if you’ve been called recently and asked about comp and scope of roles.  The most important parts here are the two I bolded – you can’t just bring in a single data point, and you also have to include detailed job scope and requirements to make your point.  If you only find one data point that supports a raise, expect your manager or HR team to counter with five that don’t.  If you bring in examples that aren’t truly comparable (the title is right, but the scope is way off, or the job requirements call for 10 years of experience when you have 5), then expect your manager to call you out on that
5. Recognize that cash compensation is only one part of the mix.  Obviously an important part, but not the only part.  Incentive compensation, equity, perks (gym membership, healthcare, etc. – they all add up!), and even company environment and lifestyle are all important considerations and important levers to pull in terms of your total compensation
6. Have the conversation in a non-emotional manner.  State your position clearly and unambiguously – you feel you deserve a raise of Q because of X, Y, and Z.  Tell your manager that you enjoy your job and the company and want to continue working there, fairly paid and amply motivated.  Don’t threaten to quit if you don’t get your way, leave the acrimony at the door, set a follow-up date for the next conversation to give your manager time to think about it and discuss it with HR, and be careful about citing your colleagues’ compensation (see next point)

The one piece of data that’s tricky to surface is internal comparables.  Even the most transparent organizations usually treat compensation data as confidential.  Now, most companies are also not idiots, and they realize that people probably talk about compensation at the water cooler.  But bringing up a specific point like “I know what Sally makes, and I make less, and that’s not fair” is likely to agitate a manager or executive because of the confidentiality of compensation.  However, as one point among many, simply asking your manager, “do you feel like my compensation is fair relative to internal comparables for both my position and performance?” and even asking questions like “which positions internally do you think are good comparables for my compensation?” are both fair game and will make your point in a less confrontational or compromising manner.

Managers, how can you best handle situations where employees come in to discuss their compensation with you?

1. Most important are two things you can do proactively here.  First, be sure to set a tone with your team that they should always be comfortable talking to you about compensation openly and directly.  That you might or might not agree with them, but the conversation is safe – remove the stigma.  Second, be proactive yourself.  Make sure you’re in touch with market rates for the roles on your team.  Make sure you’re rewarding high performers with more responsibility and more money.  And make sure you don’t let “job scope creep” happen where you just load up your good people quietly with more responsibility and don’t officially change their scope/title/comp
2. If the employee does not more or less follow the steps above and approach this in a planful, non-emotional way, I’d suggest stopping him before the conversation gets more than one or two sentences in.  Empathize with his concern, hand him a copy of this blog post, and tell him to come back in a week ready to talk.  That saves both of you from an unnecessarily uncomfortable conversation, and it gives you time to prepare as well (see next item)
3. If the employee does more or less follow the steps above and approaches this rationally, then listen, empathize, take good notes, and agree to the follow-up meeting.  Then sit with your manager or department head or HR to review the data surfaced by the employee, develop your own data-driven perspective, and respond in the meeting with the employee with data, regardless of your response.  If you do give a raise, the data makes it less about “I like you.”  If you don’t, you can emphasize the employee’s importance to you and steer the discussion towards “how to make more money in the future” by expanding role scope or improving performance

I hope this advice is helpful for both managers and employees.  Compensation is a weird topic – one of the weirdest at companies, but it need not be so awkward for people to bring up.

I wrote a little bit about the experience of being a multi-time founder in this post where I talked about the value of things like a hand-picked team, hand-picked cap table, experience that drives efficient execution, and starting with a clean slate. The second lap around the track (and third, and fourth) is really different from the first lap.

Based on what we do at Bolster, and my role currently, I spend a lot of time meeting with CEOs of all sizes and stages and sectors of company, as they’re all clients or prospects or people I’m coaching. Lately, I’ve noticed a distinct set of work and behaviors and desires among CEOs who are multi-time founders and operators that is different from those same things in first-time founders. Not every single multi-time founder has every single one of these traits, but they all have a majority of them and form a pretty common pattern. I’ve noticed this with non-profit founders as well as for-profit ones.

• They have an Easier Time Recruiting team members and investors. That may sound obvious, but there are significant benefits to it. They also tend to have Much Cleaner Cap Tables, because they lived the horrors of a messy cap table when they exited their last company without thinking about that topic ahead of time!
  
• They have a Big Vision. Once you’ve had an exit, whether successful or not or somewhere in between, you don’t want to focus on something niche. You want to go all-in on a big problem.
  
• They are interested in creating Portfolio Effect. A number of repeat founders want to start multiple business at the same time, are actually doing it, or are creating some kind of studio model that creates multiple businesses. Once you have a big team, a track record with investors, and a field of deep expertise, it’s interesting to think about creating multiple related paths (and hedges) to success.
  
• They are driving to be Efficient in Execution and Find Leverage wherever they can. One multi-time founder I talked to a few weeks ago was bragging to me about how few people he has in his finance team. At Bolster, our objective is to build a big business on a small team, looking for opportunities to use our own network of fractional and project-based team members wherever possible.
  
• They are Impatient for Progress. While being mindful that good software takes time to build no matter how many engineers you hire, repeat founders tend to have fleshed out their vision a couple layers deep and are always eager to be 6 months ahead of where they are in terms of execution, which leads me to the next point, that…
  
• They are equally Impatient for Success (or Failure). More than just wanting to be 6 months ahead of where they are in seeing their vision come to life, they want to get to “an answer” as soon as possible. No one likes wasting time, but when you’re on your second or third company, you value your time differently. As a friend of mine says in a sales context, “The best answer you can get from a prospect is ‘yes’ – the second best answer you can get is a fast ‘no’.” The same logic applies to success in your nth startup. Succeed or Fail – you want to find out fast.
  
• They are Calm and Comfortable in Their Own Skin. At this stage in the game, repeat founders are more relaxed. They know their strengths and weaknesses and have no problem bringing in people to shore those things up. They know that if things don’t work out with this one, there’s more to life.
  
• They are stronger at Self Management. They are more efficient. They exercise more. They sleep more. They spend more time with family and friends. They work fewer hours.

Anyone else ever notice these traits, or others, in repeat founders?