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Know When to Walk Away: A Guide for Fractional Leaders

I've caught myself saying the following more times than I can count: "Fractional work allows me to have all the fun associated with working at a startup without the bullsh*t associated with a startup." For most of my career, that has been true. But based on a recent experience, I have started thinking about the times when the bullsh*t of a startup does rear its ugly head and how I could advise new fractionals on how I've approached it. Here’s my list for how to know when to walk away. Reasons to Walk One of the most powerful concepts that I learned in that time is the concept of "firing a customer." There are many reasons why you might need to let a customer go: Nonpayment or chronic late payment; Violation of terms and conditions—for example, work outside scope; Unreasonable demands or expectations—3 AM replies; Abusive behavior; Lack of engagement—they forget they hired you; Misalignment of a target market; Merger and acquisitions; Legal reasons; Strategic

A Functional Fractional: How to Operate Effectively as a Fractional Executive

Working as a fractional executive isn’t for the faint of heart (if you’re considering this path, check out this post to see if fractional is right for you). There are the obvious prerequisites: years of experience, proven expertise, and executive presence. However, having skills and time in the seat isn’t enough to thrive due to the fact that a fractional executive, by definition, operates differently than someone in a full-time position.

A great fractional executive must have a strong operational foundation and thoughtful toolkit to be most effective in their engagements and maintain their work/life sanity.

While there is a healthy dose of personal preference in how each fractional executive operates, there are two primary areas to consider regardless of specialty:

  • Personal Operations—Keeping yourself organized
  • Client Operations—Integrating quickly and effectively in your engagements

Personal Operations Toolkit

A primary factor that defines a fractional executive’s experience is the number of accounts and logistics they’re juggling on a day to day basis, especially if they have more than one client engagement.

Communication Management

Most fractionals have, at a minimum, personal and business email accounts, then will receive an email account for each engagement (being entrenched in a client’s workspace is a key differentiator for fractionals vs external consulting models). Between inboxes, Slack and chat apps, collaboration platforms, etc., it’s essential to set up a system that keeps each workspace distinct and manageable.

Tool(s): Free solutions like Google Chrome Profiles or paid integrated inboxes like Superhuman can be helpful in keeping conversations straight to ensure responses are timely and commitments are met.

Calendar Management

The calendar dance is often a rude awakening for a first time fractional executive. If you’re not careful, it’s easy to inadvertently double and triple book time slots across multiple accounts or worse, miss meetings altogether.

Tool(s): There are several tools available from free to premium that integrate multiple calendars so you can schedule across numerous accounts with confidence. In fact, many now have a scheduling link feature built in for convenience. 
Pro tip: time blocking is a fractional’s best friend to minimize context switching and create consistency, but that’s a topic for another post.

Administrative Tasks

From time tracking to invoicing, getting paid is no longer as simple as it was during salaried years. Most fractionals will agree that a retainer or set fee model is a much preferred path to revenue vs hourly engagements, but either way it’s important to have a clear way to account for time spent and receive payment for services.

Tool(s): It’s wise for a fractional executive to set up their own HRIS and/or accounting platform to manage payroll, taxes, and other administrative logistics. Use a browser plugin if you need detailed logging of hours and/or add notes to your calendar to audit how your days are spent.

Client Operations Toolkit

Getting started with a new client in a fractional capacity is an exciting time. While there are many similarities to the onboarding experience of a salaried employee, there are several best practices the fractional and client should align on up front to ensure mutual success.

Expectation of Availability and Responsiveness

In many ways, a fractional executive feels like a full member of the team. However, since it’s typically not a full-time engagement, it’s important to establish up front when you’re working and when responses may be delayed.

Tool(s): Set dedicated working days/times as a baseline and communicate them clearly. Establish SLAs for responsiveness both inside and outside working hours, and be up front when responses might be delayed (e.g should they expect answers on nights/weekends or not until business hours?). If applicable, align on escalation protocols in case you’re needed for an emergency like a platform outage or security breach.

Onboarding and Ownership

A client holds some responsibility for getting a fractional up to speed, but a great fractional executive has tried-and-true methods to onboard quickly and make an impact. Remember, most companies hire fractionals not only for their skills but for their leadership and seniority so a prescriptive approach will save everyone time and effort (and lock in glowing referrals for future business).

Tool(s): Create a standard list of discovery questions to quickly learn who is responsible for core functions (perhaps even creating a RACI if one doesn’t exist), how to access and navigate systems and tools (and identify systems gaps, as applicable), and establish your domain of influence to know where your time should be spent.

In Summary

There are as many nuances to effective fractional operations as there are fractional executives. To ensure each of your engagements is successful, take the time to streamline your personal toolkit and define how you work best with your clients. Once you’ve established your operational foundation, you’ll be able to focus on the reason you pursued fractional work in the first place: delivering maximum impact while maintaining a flexible lifestyle.


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