(This post was written by my colleague Bethany Crystal and originally published on the Bolster blog yesterday. While I am still trying to figure out what posts to put on this blog vs. Bolster’s blog since the blogs are pretty similar, I will occasionally run something in both places.)

At Bolster, we believe that 2021 will mark the rise of the on-demand economy for executives. More than ever before, executives are seeking out roles that distinctly aren’t full-time for a variety of reasons – they’re in between full-time roles and want to stay engaged and meet a wide range of potential employers; they’re retired or semi-retired/post-exit and want to keep working, just not full-time; they’re fully employed but are looking for advisory opportunities to help others; or they are committed to the more flexible lifestyle that being an on-demand affords. As business leaders, you might be wondering how to take advantage of this trend and incorporate on-demand talent onto your existing team. Don’t worry – we’ve got you covered.

Let’s start with a quick primer on the distinct types of on-demand talent. Here are the four most common themes we see among our member network at Bolster:

The Four Types of On-Demand Talent

1. Interim: Someone who is partially or fully dedicated to working with your company, but only temporarily (you can think of them as “filling a gap”)
2. Fractional: Someone who works part-time (or “fractionally”) with your company on an ongoing basis (they “own” the function on a long-term, part-time basis)
3. Advisor or Coach: Someone who supports your existing team by offering external advising, coaching, or mentorship as needed (this might be on a temporary or long-term basis)
4. Project-Based: Someone who is brought on to complete a specific project or a fixed span of work (this is the closest to typical consulting work)

Depending on your business needs, the capacity of your existing team, and your resourcing, you might find it useful to have one or more on-demand executives in the mix at any given time. We’ve also found this can be a great way to keep things fresh at the leadership level and make sure new ideas are circulated with some regularity.

Business Opportunities for On-Demand Talent

While every company’s on-demand talent needs will vary, we’ve already seen a few patterns emerge from the 2,000 executives in our member network. Here are a few times to think about bringing on-demand work to your business.

Choose interim work if you need…

• A temporarily placeholder at the exec level
  Whether unexpected or planned, transitions at the executive level can come with a high cost: Any week that goes by with an unfilled seat adds more work to the team, contributes to business lag, or both. While full executive searches can take six months (or more!) to get right, many CEOs find it helpful to bring on interim help as a “stopgap” in the meantime. The most obvious benefit of interim on-demand work is to prevent your business from falling behind in areas where you may not have a deep bench below the executive level. And you might also consider that bringing in a seasoned professional as you conduct your full-time search will give your team a proxy to compare against, making that placement process a bit easier. Last – while it’s not a guarantee, there’s always the chance that your interim hire is a great fit for you and wants to stick around for the long term! You then benefit from an on-the-job “interview” or audition.
• Surge capacity staffing
  Imagine a situation where your business doesn’t need an executive in a particular function. You’re small, scrappy, and you’re getting along perfectly well with the team you have in place – and you can fill in the bits of executive leadership required for that function yourself from time to time. But then something pops up where you need to be the CEO and can’t afford to ALSO be the CXO. An interim CXO could be the right solution. For example, the 3-5 months run-up to a Series A or B financing could be a good time to bring on an experienced CFO if your only relevant team members are handling AP, AR, and Payroll. Or you could be working on your company’s public launch with a less experienced marketing team and an agency – and an interim CMO could make all the difference between success and sideways.
• Parental leave coverage
  With a growing business trend of increased parental leave coverage, CEOs are starting to use interim executives to fill holes that might temporarily exist on the leadership team. Interim work is particularly useful if there isn’t an obvious “second in command” role on that team who might take on a stretch project in their absence. Implemented correctly, bringing on an interim exec can also help to squash any fears of “getting replaced” while someone is away on leave. As an added bonus, bringing in a new face (if only temporarily) can give the remaining team a chance to “try out” a new leadership style and share feedback about what worked and didn’t work during the interim period.

Choose fractional work if you need…

• A seasoned professional’s experience and skillset (but not all the time)
  Before every full-time leadership hire, there is the sticky “in between” period of need. That’s the period when some work starts piling up, but not quite enough to fill an entire work week for one person at the executive level – or the period when you know you need a more seasoned leader in a function but just can’t afford one full-time. If you don’t have an experienced executive in the role, you miss opportunities for effectively setting up scalable practices and processes. Often, a lack of senior focus in a functional area means that you miss strategic opportunities, and sometimes it also means that you expose yourself to risk that could be avoided with the right person having ownership of the function. This is the perfect time to introduce fractional work to your business. The most classic example of fractional executive talent is the CFO who oversees the bookkeeping and accounting for several companies at once. But you can find a fractional executive for just about anything. You might consider this type of on-demand executive if you don’t yet have anyone in that functional area, if you have a team of less experienced specialists or even a more junior generalist leader in that functional area, if you want a taste of what it’d be like to dedicate more resources there, or if you need just a few things done right, without having to think about them yourself.

Choose advisory or coaching work if you need…

• Mentorship for your current executives
  Sometimes it’s helpful to see what “great” looks like in order to achieve greatness yourself. If you’re looking for a way to give a current leader an added boost to their development plan, consider bringing on someone who can serve as a mentor or advisor on a temporary or long-term basis. Someone who has been in your shoes before and can give advice and guidance based on their experience. This on-demand exec role has two big benefits: The first being that it demonstrates to your executive team that you’re committed to their ongoing success and growth, which boosts morale (and hopefully performance). The second is that you’ll be able to equip your current team with the tools they each need to scale instead of having to bring on a new wave of executives for each business stage. The advisor or coach usually works a few hours per month, once they’ve set up a strong coaching relationship.
• Access to top talent without the full-time price tag
  Just as remote work unlocked the potential to find “the best of the best” without geographic constraints, on-demand work does the same at the executive level. More and more, we’re seeing CEOs incorporate advisors to their business as a way to gain exposure to best in class talent (at a fraction of the cost). This can be a great way to introduce subject matter or functional expertise into your organization without committing to a full-time salary.

Choose project work if you need…

• A fixed-scope expert engagement at the executive level
  Just as tools like Task Rabbit made it possible to find experts to accomplish tasks on a personal level (such as moving furniture or painting a bedroom), on-demand talent makes it possible to find seasoned executives to complete one-off projects at an expert level. That’s why, on Bolster, we ask each each member to indicate what roles they can take on, and also what projects they can be hired to do. As a CEO, you might consider outsourcing some of the crunchy stuff at the exec level that might take a lot of time, or in cases where you need a quick turnaround to get to an MVP. Common projects we’ve seen to date include building sales commission plan structures, designing a go-to-market launch plan for a new product, running due diligence on an acquisition, overhauling pricing and packaging, working on a strategic plan, TAM analysis, budgeting process, or creating a diversity & inclusion strategy for the company.
• An experimental project that won’t distract the current team
  One final area where you might consider on-demand work is for a project that feels more like an addendum to your current business, or an early experiment. At Bolster, we brought on an on-demand executive to help us think through and roll out a brand new product that we’re in the early days of testing right now. We’ve seen other CEOs use project-based work at the exec level for things like evaluating market expansion possibilities or speccing out the MVP of a potential new product.

This is just a short list of some of the possibilities where on-demand talent might support you in your business today. One of our favorite parts about this type of work is just that – the flexibility it offers to you and your team. Whether your business is just getting started or if you’re operating on all cylinders, don’t forget to consider on-demand work as part of your CEO toolkit for this year and beyond.

– Bethany Crystal, February 2, 2021

The Best Place to Work, Part 0

I keep getting questions about a deck I’ve used several times at Techstars, Seedcamp, DreamIt, and the like which is called “7 Ideas for Creating the Best Place to Work.”  So today I will launch a 7-part series over the next 7 weeks to describe my 7 points.  As always, this is not intended to be perfect or comprehensive, but it is a bit of lessons learned over the last 12-13 years at Return Path.  It’s just 7 ideas – not the only 7 ideas.  And there’s nothing magic about the number 7, despite what George Costanza says.  Or Steven Covey.

Here’s the outline:

1. Surround yourself with the best and brightest
2. Create an environment of trust
3. Manage yourself very, very well
4. Be the consummate host
5. Be the ultimate enabler
6. Let people be people
7. Create a thankful atmosphere

Let’s go!  I will create a tag cloud for this series called Best Place to Work.

What Kind of Entrepreneur Are You?

I think there are two kinds of entrepreneurs, and sometimes, you can be both.  There is the kind that starts businesses, and there is the kind that builds businesses.

The kind of entrepreneur who starts businesses but usually doesn’t like running or building them are typically serial entrepreneurs.  How can you spot one?  They:

• Have an idea a minute and a bit of ADD – they are attracted to bright shiny objects – they can’t focus
  • Would rather generate 1 good and idea and 19 bad ones than just 1 good one
  • Are always thinking about the next thing, only excited by the possibility of what could be, not by what is
  • Are more philosophical and theoretical than practical
  • Probably shouldn’t run businesses for more than a few months
  • Are likely to frustrate everyone around them and get bored themselves
  • Are really fun at cocktail parties
  • Say things like “I thought of auctions online way before eBay!”

The second kind of entrepreneur is the kind of person who can run businesses but may or may not come up with the idea.  Typically, these people:

• Care about success, not about having the idea
• Love to make things work
• Would rather generate 1 idea and execute it well than 2 ideas
• Are problem solvers
• Are great with people
• May be less fun at cocktail parties, but you’d want them on your team in a game of paintball or laser tag

It’s the rare one who can do both of these things well.  But you know them when you see them.  Think Dell or Microsoft…or even Apple in a roundabout way if you consider the fact that Jobs hired Cook (and others) to partner with them to run the business.

OnlyOnce, Part II

After more than six years, my blog starting looking like, well, a six-year old blog on an off-the-shelf template.  Thanks to my friends at Slice of Lime, OnlyOnce has a new design as of today as well as some new navigation and other features like a tag cloud and Twitter feed (and a new platform, WordPress rather than Typepad).  I know many people only read my posts via feed or email (those won’t change), but if you have a minute, feel free to take a look.  The site also has its own URL now – https://onlyonceblog.wpengine.com.

With my shiny new template, I may add some other features or areas of content over time, as well.  There are still a couple things that are only 95% baked, but I love the new look and wanted to make if “official” today.  Thanks to Kevin, Jeff, Mike, Lindsay, and everyone at Slice of Lime for their excellent design work, and for my colleague Andrea for helping do the heavy lifting of porting everything over to the new platform.

First day at Techstars:  Where do you start?

I’m a new mentor this year at Techstars, a program in its third or fourth year in Boulder (and this year also in Boston for the first time) that provides a couple dozen companies with seed capital, advice and mentorship, and summer “incubation” services in a really well conceived for-profit venture started by David Cohen in Colorado.

Yesterday was my first day up there with my colleague George Bilbrey, and we met with three different companies, two of which we will tag team mentor through the summer.  I won’t get into who they are at the moment, mostly because I’m not sure what the confidentiality issues are offhand, but I’ll make the first of a series of posts here about observations I make from doing this work.

Yesterday’s thought was:  Where do you start?

It was so interesting to meet with in some cases pretty raw companies.  They weren’t exactly “a guy with an idea,” but for the most part they were <5 person teams with a working code base and some theories about who would buy the product. 

So where do you start on the question of business planning.  Do you dive into the deep end of details?  (What should we charge?  How do I get my first 5 beta customers?  What about this new feature?)  Or do you wade into the shallow end of methodical planning?  (Who is our target market?  What problem are we solving?  How much is it worth to the prospect?  What will it cost us to produce, sell, and support the product?)  We heard both of those approaches yesterday across the three companies. 

My conclusion isn’t that there’s a single correct answer.  For most mortals, it’s probably the case that while it’s good to have a product and an inspiration behind it, there’s a long road between that and a successful company that requires careful articulation of the basics and a good grip on potential economics before incremental investments of time or money. 

But there are the occasional companies whose ideas are so perfectly timed for such a large market or user base that some of the method can be ditched up front in the name of getting to market (think Twitter or eBay) — provided that the company circles back to those basics down the road in order to grow smartly over time.

Anyway, it was a thought-provoking day and great to see new entrepreneurs and ideas take root.  George and I have a series of six sessions set up with these companies as well as the full Techstars Demo Day in early August.  I’ll try to blog some thoughts after each session.

Fred beat me to it. I wasn’t at a computer to post this yesterday on the actual 4th of July, so today will have to do. I’ve read lots of books on the American revolution and the founding fathers over the years. It’s absolutely my favorite historical period, probably because it appeals to the entrepreneur in me. Think about what our founding fathers accomplished:

– Articulated a compelling vision for a better future with home democratic rule and capitalist principles. Life, liberty, and the pursuit of happiness is really the ultimate tag line when you think about it.

– Raised strategic debt financing from, and built critical strategic alliances with France, the Netherlands, and Spain.

– Assembled a team of A players to lead the effort in Washington, Adams, Jefferson, Franklin, Hamilton, and numerous others who haven’t been afforded the same level of historical stature.

– Built early prototypes to prove the model of democratic home rule in the form of most of the 13 colonial assemblies, the Committees of Correspondence, and the Articles of Confederation.

– Relentlessly executed their plans until they were successful, changing tactics several times over the years of 1774-1783 but never wavering from their commitment to the ultimate vision.

– Followed through on their commitments by establishing a new nation along the principles to which they publicly committed early on, and taking it to the next level with the Constitution and our current form of government in 1789.

And let’s not forget, these guys accomplished all of this at a time when it took several days to get a letter from Virginia to Boston on horseback and six weeks to get a message across the Atlantic on a sailboat. Can you imagine what Washington would have been able to accomplish if he could have IMd with Adams in Paris?

So happy 4th to all, with a big thanks to this country’s founding fathers for pulling off the greatest spin-off of all time.

What Kind of Entrepreneur Do You Want to Be?

I had a great time at Princeton reunions this weekend, as always.  As I was talking to random people, some of whom I knew but hadn’t seen in a long time, and others of whom I was just meeting for the first time, the topic of starting a business naturally came up.  Two of the people asked me if I thought they should start a business, and what kind of person made for a good entrepreneur.

As I was thinking about the question, it reminded me of something Fred once told me — that he thought there were two kinds of entrepreneurs:  people who start businesses and people who run business. 

People who start businesses are more commonly known as serial entrepreneurs.  These people come up with ideas and love incubating them but may or may not try to run them longer term.  They:

– generate an idea a minute
– have a major case of ADD
– are easily distracted by shiny objects
– would rather generate 1 good and idea and 19 bad ones than just 1 good one
– are always thinking about the next thing
– are only excited by the possibility of what could be, not what is
– are more philosophical and theoretical
– probably shouldn’t run the companies they start for more than a few months, as they will frustrate everyone around them and get bored themselves
– are really fun at cocktail parties
– say things like “I thought of auctions online way before eBay!”

The second type of entrepreneur is the type who runs businesses (and may or may not come up with the original idea).  These people:

– care about success, not just having the idea
– love to make things work
– would rather generate 1 idea and execute it well than 2 ideas
– are problem solvers
– are great with people
– are maybe less fun at cocktail parties, but
– you’d definitely want them on your team in a game of paintball or laser tag

Neither one is better than the other, and sometimes you get both in the same person, but not all that often.  But understanding what type of entrepreneur you are (or would likely be) is probably a good first step in understanding whether or not you want to take the plunge, and if so, what role you’d like to play in the business.

A Better Way to Shop

I love Zappos.com.  It’s rapidly becoming the only place I buy shoes.  Their web site experience is ok – not perfect, but pretty good, but their level of service is just unbelievable.  They are doing for e-commerce (shoes in particular) what Eos is doing for air travel.

They’re always great at free shipping and have always been super responsive and very personal and authentic when it comes to customer service.  But today took the cake.  I emailed them when I placed an order for new running shoes because I also wanted to buy one of those little “shoe pocket” velcro thingies that straps onto shoelaces and holds keys and money for runners.  I didn’t find one on the Zappos site and just asked if they carried the item in case I missed it.

Less than 24 hours later, I got an email reply from Lori, a Customer Loyalty Representative there, who apologized for not carrying the item — and then provided me with a link to buy it on Amazon.com which she had researched online herself.

Zappos’s tag line on their emails says it all:

We like to think of ourselves as a service company that just happens to sell shoes.

Does your company think of itself and its commitment to customer service like that?

I Don’t Want to Be Your Friend (Today)

The biggest problem with all the social networks, as far as I can tell, is that there’s no easy and obvious way for me to differentiate the people to whom I am connected either by type of person or by how closely connected we are.

I have about 400 on Facebook and 600 on LinkedIn.  And I’m still adding ones as new people get on the two networks for the first time.  While it seems to people in the industry here that “everyone is on Facebook,” it’s not true yet.  Facebook is making its way slowly (in Geoffrey Moore terms) through Main Street.  Main Street is a big place.

But not all friends are created equal.  There are some where I’m happy to read their status updates or get invited to their events.  There are some where I’m happy if they see pictures of me.  But there are others where neither of these is the case.  Why can’t I let only those friends who I tag as “summer camp” see pictures of me that are tagged as being from summer camp?  Why can’t I only get event invitations from “close friends”?  Wouldn’t LinkedIn be better if it only allowed second and third degree connections to come from “strong” connections instead of “weak” ones?

It’s also hard to not accept a connection from someone you know.  Here’s a great example.  A guy to whom I have a very tenuous business connection (but a real one) friends me on Facebook.  I ignore him.  He does it again.  I ignore him again.  And a third time.  Finally, he emails me with some quasi-legitimate business purpose and asks why I’m ignoring him — he sees that I’m active on Facebook, so I *must* be ignoring him.  Sigh.  I make up some feeble excuse and go accept his connection.  Next thing I know, I’m getting an invitation from this guy for “International Hug a Jew Day,” followed by an onslaught of messages from everyone else in his address book in some kind of reply-to-all functionality.  Now, I’m a Jew, and I don’t mind a hug now and then, but this crap, I could do without. 

I mentioned this problem to a friend the other day who told me the problem was me.  “You just have too many friends.  I reject everyone who connects to me unless they’re a really, super close friend.”  Ok, fine, I am a connector, but I don’t need a web site to help me stay connected to the 13 people I talk to on the phone or see in person.  The beauty of social networks is to enable some level of communication with a much broader universe — including on some occasions people I don’t know at all.  That communication, and the occasional serendipity that accompanies it, goes away if I keep my circle of friends narrow.  In fact, I do discriminate at some level in terms of who I accept connections from.  I don’t accept them from people I truly don’t know, which isn’t a small number.  It’s amazing how many people try to connect to me who I have never met or maybe who picked up my business card somewhere.

The tools to handle this today are crude and only around the edges.  I can ignore people or block them, but that means I never get to see what they’re up to (and vice versa).  That eliminates the serendipity factor as well.  Facebook has some functionality to let me “see more from some people and less from others” — but it’s hard to find, it’s unclear how it works, and it’s incredibly difficult to use.  Sure, I can “never accept event invitations from this person,” or hide someone’s updates on home page, but those tools are clunky and reactive.

When are the folks at LinkedIn and Facebook going to solve this?  Feels like tagging, basic behavioral analysis, and checkboxes at point of “friending” aren’t exactly bleeding edge technologies any more.

I was excited to read Launchpad Republic: America’s Entrepreneurial Edge and Why It Matters, by Howard Wolk and John Landry the minute Brad sent it to me. I love American history, I love entrepreneurship, and I’m deeply concerned about the health of our country right now. I have to say…on all fronts, the book did not disappoint!

The authors make several points, but the one that sets the tone for the book is that like our country’s origins and culture in general, entrepreneurship is itself rebellious. It’s about upstarts challenging the status quo in some way or other with a better way to do something, or with a new thing. The balance between protecting private property rights and allowing for entrepreneurs to fail and to disrupt incumbent leaders is what makes America unique, especially compared to the way European business culture has traditionally operated (consensus-oriented) and the way China operates (authoritarian).

I loved how the authors wove a number of business history vignettes together with relevant thru lines. Business in Colonial times and how Alexander Hamilton thought about national finances may seem dusty and distant, but not when you see the direct connection to John D. Rockefeller, IBM, GE, Microsoft, or Wendy Kopp.

The book was also a good reminder that some of the principles that have made America great and exceptional also underly our successful business culture, things like limited government, checks and balances within government and between government and the private sector, and decentralized finance.

Without being overly political, the authors also get into how our political and entrepreneurial system can and hopefully will tackle some of today’s more complex issues, from climate change to income inequality to stakeholder capitalism.

At the heart of all of it is the notion that entrepreneurs’ creativity drive America forward and are a leading force for making our country and our economy durable and resilient. As a career entrepreneur, and one who is now in the business of helping other entrepreneurs be more successful, this resonated. If you’re a student of American history…or a student of entrepreneurship, this is a great read. If you’re both, it’s a must read.

Across 22 years and two companies now, our system of giving performance feedback has evolved significantly. I thought I’d take a pass at chronicling it here and seeing if I had any learnings from looking at the evolution. Here’s how things evolved over the years:

• Written performance reviews. The first year of Return Path, we had a pretty standard process for reviews. They were more or less “one-way” (meaning managers wrote reviews for their direct reports), and they only happened annually.
• Written 360 reviews. We pretty quickly moved from one-way reviews to 360s. I wrote about this here, but we always felt that being able to give/receive feedback in all directions was critical to getting a full picture of your strengths and weaknesses.
• Live 360 reviews. In addition to the above post/link, I wrote about this a bit further here and here. The short of it is that we evolved written 360s for senior leaders into facilitated live conversations among all the reviewers in order to resolve conflicting feedback and prioritize action items.
• Live 360 reviews with the subject in the room. I wrote about this here…the addition of the subject of the review into an observer/clarifying role present for the facilitated live conversation.
• Peer feedback. At some point, we started doing team-based reviews on a regular cadence (usually quarterly) where everyone on a team reviews everyone on a team round-robin style in a live meeting.

The evolution follows an interesting pattern of increasing utility combined with increasing transparency. The more data that is available to more people, the more actionable the feedback has gotten.

The pluses of this model are clear. A steady diet of feedback is much better than getting something once a year. Having the opportunity to prioritize and clarify conflicts in feedback is key. Hearing it firsthand is better than having it filtered.

The biggest minuses of this model are less clear. One could be that in round robin feedback, unless you spend several hours at it, it’s possible that some detail and nuance get lost in the name of prioritization. Another could be that so much transparency means that important feedback is hidden because the people giving the feedback are nervous to give it. One thing to note as a mitigating factor on this last point is that the feedback we’re talking about coming in a peer feedback session is all what I’d call “in bounds” feedback. When there is very serious feedback (e.g., performance or behavioral issues that could lead to a PIP or termination), it doesn’t always surface in peer feedback sessions – it takes a direct back channel line to the person’s manager or to HR.

The main conclusion I draw from studying this evolution is that feedback processes by design vary with culture. The more our culture at Return Path got deeper and deeper into transparency and into training people on giving/receiving feedback and training on the Difficult Conversations and Action/Design methodologies, the more we were able to make it safe to give tough feedback directly to someone’s face, even in a group setting. That does not mean that all companies could handle that kind of radical transparency, especially without a journey that includes increasing the level of transparency of feedback one step at a time. At Bolster, where the culture is rooted in transparency from the get go, we have been able to start the feedback journey at the Peer Feedback level, although now that I lay it out, I’m worried we may not be doing enough to make sure that the peer feedback format is meaningful enough especially around depth of feedback!