Derek Sidebottom

Leadership Coach


Derek Sidebottom

President, FarsideHR Solutions


San Francisco  Austin  Toronto

Derek is a 20+ year high growth HR executive with extensive operating, consulting and product management experience.

Since our founding in 2014, FarsideHR’s mission has been to Make Managers Awesome. We help managers and executives at all levels take the leadership leap

The Leadership Fitness Resolution

When it comes to your physical fitness, there’s an inconvenient truth. Despite all the ‘get rock hard abs fast’ headlines, going to the gym once a year achieves nothing. Equally. There is an inconvenient truth when it comes to your leadership fitness.

Despite all the listicles, books and simplified ‘thought leader’ headlines, setting direction and assessing performance once a year also achieves nothing. It’s all too easy to cut corners and fall out of shape. That is, until milestones are missed and your best people are leaving. As with your health, acute leadership health incidents are often entirely preventable through lifestyle change.

Your Success Starts With: You Have to Want It.

Agile Goals. Fluid Distributed Teams. The workforce is increasingly acting like a fluid vs. a solid. Where once upon a time the traditional departmental hierarchy was the most common organizational structure, we’re now seeing that work is being organized across a changing network of employees, contractors, temps and gig workers who are distributed around the globe. The classic storming, forming and norming model for change management seems archaic. It’s now how will we manage perpetual storming?

Connecting people to purpose to drive results relies more than ever on exceptional leadership and a strong management bench ready to manage change. Balancing the supply and demand of the worldwide productivity marketplace occuring daily in every organization has no ‘quick win’ formula; priorities shift quickly and distributed personnel are more mobile than ever. Like all-star athletes who commit to rigorous diet, strength and cardio routines, all-star leaders must hone and perfect their own personal leadership fitness 

routines to drive results and engage top talent.

Is There an Optimal Routine?

In late Q4 2019 we at FarsideHR began The Distributed Workforce Project. We asked a series of senior personnel to 1) think about the best, most high performing teams they have ever been part of and 2) what did their leader do to make the team so memorably high performing? To ensure we focused on the most chaotic end of the spectrum so as to isolate the most effective routines, we further refined the ask to only distributed teams where people were not all co-located in the same office. Our research originated on the premise that the future of work will increasingly rely on contingent, gig and distributed workers as the millennial workforce demands more flexibility and begins to leave high cost urban locations.

We’re still analyzing the results. But thus far we’re not surprised. This primary research on high performing distributed teams is reinforcing our experience working with top employer award winners and decades of working inside hyper-growth Silicon Valley organizations.

High performing leaders of complex, distributed teams (as reported by team members themselves) tend to continuously answer the following core questions exceptionally well on a recurring basis:

  • Purpose:Why are we here and why is it worthy of our time?
  • Priorities:What are we doing & how is it all connected?
  • Accountability:Who is doing what and when?
  • Feedback:Are we creating the right inclusive feedback culture and mechanisms to stay on track and continuously improve?
  • 1:1 Coaching:How do we help every employee understand their role and how to be successful?
  • Career Development:It’s a two way exchange of value, how can we ensure our best talent chooses to learn, improve and grow with us vs our competition?

When asked to stack rank, connecting to a higher purpose and goal clarity took the #1 and #2 spots respectively. But I ask you to read these themes and self score your own leadership fitness levels. Do your teams or team of teams feel a strong connection to an inspired vision, mission & values? Are cascading goals, roles & accountability frameworks effective and refreshed regularly? Are you fostering a learning environment anchored in a culture of feedback? Is every manager beneath you investing in personalized meaning and coaching with their staff? Are you truly supporting personal learning and growth?

“He made each member of the team (remote or local) understand their

mission and importance to the desired outcome, tailoring motivational

anecdotes to be relatable to each member”

The Distributed Workforce Project – FarsideHR Solutions

While the response patterns were remarkably consistent around what great leaders did well. There were definite shout outs and preferences for servant-leader style and how genuine & inclusive the leader was as they went about their routines. This reinforced the notion that it’s not just ‘What’ you do, it’s also ‘How’ you do it.

Leadership Lifestyle Change

Unfortunately, it’s not enough to write things down and go through the motions a few times. The strategy/execution gap is littered with expensive facilitated strategic plan wall art that *sometimes* makes it back to the team in the form of a presentation.

Looking deeper at the dysfunction, rarely is ownership and accountability for top level targets (let alone supporting objectives and goals) successfully transferred to the real owners or updated in real time to measure progress. Why and What needs to be connected to dynamic Who, When and How through modern technology so as to process and display the sum of all the changed variables – an agile plan of record.

Routine. Technique. Technology.

The stakes are high. Getting a trainer to master the 6 core routines and investing in the right technology to support them at scale is a critical investment in you, your investors, your customers and your team. It’s worth it. And the future of work actually makes it necessary as the pace of change accelerates.

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