Bolster
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Lessons Learned from Joining Bolster as Fractional Employees

As an on-demand marketplace, we spend a lot of time at Bolster thinking about how CEOs can leverage interim, fractional, and project-based work to augment their teams and achieve scale faster. There are a lot of benefits to working with on-demand talent (and a lot of ways to use it). One model we’ve been using at Bolster is a “try before you buy” approach. When new leaders join the company, we offer the option: How about we start in a fractional capacity before becoming full-time?

Along with my colleagues Micah Mador, who works with me on our portfolio partnerships and community, and Jimmy Davis on our product team, this is the approach we all took when joining Bolster. This was the first time any of us had worked in a fractional capacity, and we learned a lot along the way.

The three of us took a moment to reflect and share the key takeaways from our first fractional jobs. While we all had unique experiences, our lessons demonstrate three critical skills to have as a successful fractional leader: Time management, clarity of role, and communication:

Micah Mador: 10-15 hours a week for one month, then 50% time for one month

  • Get really, really good at calendaring (and inbox management).
    Initially I thought I could spend 2-3 days a week on “Bolster time” and pause that work during the rest of the week, but splitting time between two jobs by days of the week didn’t work. I found myself wanting (and needing) to be more responsive. I was trying to minimize context switching but realized it’s inevitable so decided to embrace it with some guardrails. I ended up starting and ending each day in each inbox and worked hard to get them to as close to zero as possible. On the tactical side, I added Bolster work blocks to my calendar as available chunks of time my new colleagues could book internal meetings with me or include me on external ones. I found that a paid Calendly account for $10/mo allows you to sync two calendars (including one in Gmail and one in Outlook) and have the app check for conflicts to avoid double bookings. Gamechanger. I could then just send my calendar link to folks knowing I wouldn’t get double booked.
  • Be clear on what you will (and won’t) do.
    Working at any startup can be a bit hectic, chaotic, and ad-hoc. Priorities can change week to week and projects can change or morph over time. As a new fractional member of the team, I wanted to pick up things and add value instantly. To be clear on expectations up front (there are only so many hours in the day/week), I outlined what I thought my role would be in my fractional capacity and shared it with the folks at Bolster to get their feedback and buy-in. It could be helpful to go through this exercise with the company or do your best to distill your conversations into a project and work scope for them to react to. Setting these expectations early on helped to keep me focused and gave me a filter to run requests or ideas through.
  • Seek first to understand, then to be understood.
    I borrowed this one from Stephen Covey’s “Seven Habits of Highly Effective People”. While it’s natural to want to come into a new company and immediately make an impact, show how you think things should work, implement new systems, etc.; it is usually a good idea to take some time to just get a feel for how things are run and people work. (Of course, in an interim or fractional capacity, the “intake time” may be a lot shorter than if you were starting a full-time role.) Some things that helped me were getting a sense of how internal meetings work (is there a set agenda or structure, shared doc for ideas, cancellation policy if there is nothing new to cover), what software tools the company used (can you “BYOT” - Bring your own tools?), how the team liked to communicate about different things and whether there was a communication hierarchy to tools (slack, email, voxer, zoom, text). I fought my natural inclination to “do” from day one and it allowed me to get a lay of the land before trying to make my mark.

Bethany Crystal: Worked at 50% time for 3 months

  • Start every day with a to-do list.
    Back in a luxurious “one job only” world, I used to spend the first hour or so of each workday sort of puttering around my inbox looking for projects to pick up. When juggling two jobs, I just didn’t have the luxury to waste that kind of time. I soon learned that the best thing I could do was to start each day with a very specific list of “what I need to accomplish today” – a sort of “solo standup,” if you will. This immensely helped me to dive right in and maximize my output on a daily basis.
  • Schedule time for deep work.
    The trickiest part for me was making sure to give myself time to actually get work done. I learned, without explicitly blocking time on my calendar for focus time and project work, meetings simply popped up from both inboxes all the time. To top it off, I was still breastfeeding my baby at two- or three-hour intervals. I felt like I was constantly getting interrupted! There were some days when I’d go eight hours straight in back-to-back Zoom meetings, then need to end my day right at 5 p.m. to feed the baby and never have time for any follow-ups. Once I realized this was a time blocking problem more than anything else, I started scheduling two-hour time windows at least 3-4 times a week for “Deep Work.” Once I identified the right proportion of time that I needed to be in “meeting work” vs. “deep work,” it was like I’d unlocked a secret bonus level for being fractional. I could finally accomplish my goals.
  • Ask yourself: What’s the job to be done? Get that thing done really well.
    Peak performance in a fractional job doesn’t look the same as it might in a full-time world. I had to remind myself more than a few times: “I’m not working two full-time jobs. I’m working two half-time jobs.” This meant fighting against my natural tendency to dive deep into every other project going on at Bolster. When I wasn’t able to direct my limited attention toward a singular focus, I’d end some days feeling frustrated when I felt I made little progress in either role. Eventually I came to realize this important axiom: Being fractional means being able to operate at a high level without needing all of the details. By reminding myself about “the job to be done” – or, the sole focus of my energy in each role – I was able to identify the signal through the noise.

Jimmy Davis: Worked 10 hours a week for 4 months

  • Manage others’ expectations regularly (and keep reminding people about it).
    Joining a 6 month old tech startup with no “official” product manager, there was no shortage of product-related work to do. It was important to set expectations and communicate what you will, and won’t, be working on each week. I’d often set goals at the beginning of each week and the 10 hours would fill up pretty quickly. Even attending a one-hour daily standup with the team ate up half of my working hours, so we switched to just three days a week. Whenever new requests would come in, it was important to be transparent about where I was spending my limited time.
  • Manage your own expectations regularly (and keep reminding yourself about it).
    There were times when I’d finish a week and feel like I wasn’t accomplishing enough and wanting to do more. I had to keep reminding myself that the amount of time I typically had in a week of work (~40-50 hrs), I was now doing in a month (10 hrs/week * 4 weeks = 40 hrs) - that took me some time to get used to. At the end of the day, I still had a full-time job that was my priority and it was great working fractionally with a team that was extremely flexible, respectful of my time and allowed me to handle meeting schedules that worked best.
  • Remember why you’re doing it.
    Prior to joining Bolster, I had been at the same startup for nearly 7 years and had been starting to think about what’s next. Working a fractional role was a perfect opportunity to dip my toes into something else before deciding to dive in (I think this is great for both sides - the fractional worker and the company). Typical fractional workers may take on multiple roles that add up to 100% - I was taking on an additional 20-25% on top of my already 100% full-time job. At times the extra 10 hours a week felt like too much (especially with a 2 year old and 3 month old when I started!) Ultimately, it was a great opportunity for me to take on a “side hustle” while also engaging in a “try before you buy” type model, and gladly it worked out well from both sides and ended in a full-time opportunity.

The three key lessons that flow across all our experience and also across the experience of other fractional executives we’ve interviewed:

  • Be intentional about your time
  • Get clarity on your role
  • Communicate effectively

Whether you’re joining a company as a fractional employee or hiring one for your first time, we hope our lessons learned will make the transition as effective and productive as possible.

- Bethany Crystal, Micah Mador, and Jimmy Davis, February 16 2021