Ben Brooks: Coaching Reimagined

Ben Brooks is the award-winning Founder and CEO of NYC-based PILOT, a coaching software that’s data-driven, mobile-enabled, and cohort-based. PILOT was named the #1 HR tech startup to watch in 2020 and won the industry’s largest pitchfest in 2019. Ben has previously held a number of leadership and management roles and is an industry leader in maximizing potential to help employees manage their own careers.  

In this episode, Ben discussed his goal to democratize coaching by making it scalable, affordable and flexible,leveraging technology. An expert on human capital, Ben helps HR teams evolve, accelerate their individual professional careers and “share in the rewards” of the impact they create.

It was a pleasure to host Ben on the show.

Ben Brooks

Ben Brooks is the Founder & CEO of PILOT, an award-winning employee coaching software product. Serving an impressive cohort of respected corporate, growth businesses, and nonprofits, PILOT is democratising coaching at scale with a mission that “everyone feels powerful at work.” PILOT was named the #1 HRTech Startup to Watch in 2020 and won the industry’s largest Pitch-fest in 2019. 

Inspired by his previous leadership and management roles in HR and his successful business & executive coaching practice, Ben saw an opportunity to democratise executive coaching by making it scalable, affordable, and flexible by leveraging technology. 

Ben was recently named 1 of HR Executive Magazine’s Top 100 HR Tech Influencers of 2019. 


Matt Burns

Matt Burns is an award-winning executive, social entrepreneur and speaker. He believes in the power of community, simplicity & technology.


Brian Sowards: Every Company is a Tech Company

Brian Sowards thinks about problems differently. His experiences as a start-up founder, in private equity, venture capital & as a strategist for some of the world’s leading technology organisations, have granted him a broader view of traditional opportunities. Now as a Global Talent Strategist & Head of Partnerships at Ph. Creative, a Liverpool-based employer brand agency, Brian is responsible for delivering fresh insight on genuine innovation with today’s most-recognisable brands and brilliant thought-leaders. Sounds fun, right?

In this episode, Brian & I discuss how these organisations are increasingly defining themselves by how they leverage technology. And where are most of them on this journey? ‘Just about to jump off the cliff’, according to Brian.

In the Age of Information, the inevitable migration to digital transformation necessitates a redefinition of trust. Decision-making is decentralised as organisations can no longer evolve at the glacial pace they once did. Change is hard. And balancing experimentation with control presents new challenges that most organisations are ill-equipped to manage. Success was once defined as having a repeatable, scalable process. Today, the new battleground is agility.

So who owns the transition?

Brian Sowards

Brian Sowards is a Talent Strategist, supporting talent leaders as they develop, present, and win buy-in for transformational initiatives. He brings breadth and depth to his work, with deep expertise in business process engineering, experience design, digital media, tech, analytics, and innovation.


Matt Burns

Matt Burns is an award-winning executive, social entrepreneur and speaker. He believes in the power of community, simplicity & technology.


Anne-Marie Headley: Brave New World

Anne-Marie Headley, an award-winning Senior HR Business Leader, Board Advisor, and Trustee has spent more than two decades transforming organizations and building high performance cultures for conglomerates like Uber and Cisco. She is also the founder of My WorkforceBuddy, a people consulting company that helps organizations scale HR infrastructure to growth initiatives. 

In this episode of Thinking Inside the Box Podcast, Anne-Marie joins host Matt Burns to discuss the importance of technology in the learning process and its impact on the learner outcomes. She also shares her views on the relevance of gender representation and diversity in leadership roles in today’s environment.

Anne-Marie Headley

Anne-Marie Headley is a Senior HR Business Leader and Founder of My WorkforceBuddy.  She has close to two decades ‘experience in the IT industry and specialises in transforming Fortune 500 companies, scaling growth companies, and building high performance cultures. Her previous role was at Cisco Systems, where she was part of the leadership team of the Service Provider Applications and Platform Group which generated revenues in excess of $1 billion.

Most recently as Head of Regional HR at Uber, Anne-Marie was responsible for people strategy, workplace culture, organisational development, governance and employee experience across Northern and Eastern Europe. She is a Board Advisor at Salary Finance, Trustee of The Legacy OnSide Youth Zone, Trustee of Reedham Children’s Trust, a Group Mentor at the Aleto Foundation and Founder of Toastmasters International for Cass Business School in London.


Matt Burns

Matt Burns is an award-winning executive, social entrepreneur and speaker. He believes in the power of community, simplicity & technology.


Put Down Your Pencils: A Message to Global HR Professionals

The world is changing. The same global forces changing the very nature of work affect the HR profession. In this age of disruption, we have a shared responsibility: to our organizations as they navigate turbulent futures & to ourselves, as we redefine the purpose of our chosen profession.

Ask the average employee what they believe HR is responsible for. You’ll hear: ‘hiring’, ‘payroll’ & ‘training’. So what’s the problem?

The tasks listed above are disappearing. Manual, repetitive, administrative tasks are being automated.

To best secure strong futures for our organizations & our profession, it’s important that we look forward. First from a ‘department’ lens – what will organizations need / expect from HR? Then from a ‘practitioner’s’ lens – what skills will we need to support those goals?

This isn’t an article about technology, though it could be. It’s true that technology holds the key to solving many of our existing challenges – talent/skills shortages, higher attrition, stretched budgets. It’s also true that the HR professional’s ability to leverage technology within their practice will become increasingly important.

However, technology is not a panacea. Blindly pairing technology with a problem, in and of itself, does not solve anything. It’s in that spirit that we’ll discuss the required future skill-sets for HR practitioners.

The Department Lens

The HR department of the future will be comprised of two core pillars: administrative & knowledge-based. The first, administrative, comprises core transactional HR functions (payroll, scheduling, records management, etc.). These tasks will largely be automated. A single resource will administer multiple programs to identify & resolve exceptions, analyze trends & produce reports. The predictable, repetitive nature of these tasks, coupled with the sensitive nature of the information, means it will be solved for in one of two ways: centralized & owned by a small number of trusted, salaried resources. Or, along with the risk & liability, the activities will be completely outsourced.

The inverse will be true for the second core pillar: knowledge-based functions. Learning design, employment branding & data science are three examples of specialized tasks that will fragment & niche out. HR Leaders who think about talent strategy differently will develop & leverage a network of knowledge-based freelancers, tasking their supervision to a single scrum master, who will ensure timeline, budget & quality metrics are met.

There’s an existing business case for this design with medium & large organizations today. Consider the following example: an industry-expert compensation consultant is benchmarking key technical roles against the local market & in tandem with an employment branding consultant, developing a talent acquisition strategy to identify & advertise to between 3 & 5 global cities with an abundance of undervalued (inexpensive) qualified candidates.

This is possible today. It requires a change in our mindset.

The Practitioner’s Lens

What does this all mean for the individual HR professional?

When I started in the HR profession 15 years ago, data was the hot-button issue. HR departments buoyed by the latest HR technologies with reporting functions began assembling beautiful scorecards to rival other corporate departments. There was a prevailing belief that we would use data to inform future organizational strategy & simultaneously demonstrate our value. We’d finally gain that ever-elusive ‘seat-at-the-table’.

Today we have the inverse problem. We don’t have an absence of data; most HR departments are drowning in it. It’s hard to know where to start.

To avoid a future dominated by the production & distribution of lagging, reactive scorecards, HR professionals must be able to quickly identify & highlight what’s really important. What are the organizations key objectives? What are its biggest risks? What does your data tell you about these two questions? Tell me a story.

We’ll need HR practitioners who can ‘flip-the-model’, synthesize, curate & translate historical data to create predictive models & share compelling stories. Both pieces are equally important: poor analysis paired with good storytelling is fluff; great analysis with poor storytelling sits in someone’s desk drawer collecting dust.

When we can consistently & proactively illuminate potential risks & solve them before they become issues, we transform our relationship with the business. We evolve from a rules-based, reactive ‘firefighting’ function – a design that allows leaders to abdicate ownership of their people – to a function that provides informed, timely, relevant counsel.

That’s how you become a trusted advisor. This is how you remain relevant in a changing landscape.

The Final Word

The world is changing. As HR leaders & practitioners, we must get informed, have a perspective & put forward a vision for change.

How? You must make time in your routine for education. Read 1-2 articles a week on the future of our profession. Learn about new HR technologies, data & how we can more adeptly blend the qualitative & the quantitative.

Develop opinions. Like me, do you believe Applicant Tracking Systems have become too impersonal? How can we make it better today?

Our organizations & the employees who bring it to life, are counting on us to speak for them. Let’s not miss that chance.

A Winning Formula: Transformation Through HR Technology

According to reports, a quarter (25%) of technology projects fail & nearly 50% need massive changes prior to completion.

Why do so many technology projects fail? The same report indicates half (54%) can be attributed to poor management, which when you think of it, makes sense. 

Technology projects are hard. You have end users with various levels of technical acumen, time & alignment. It’s one of the many reasons we’ve witnessed the proliferation of change management theory & professionals. Change is hard.

I’ve led & supported multiple HR technology projects. In 2016, while leading the HR function at JYSK, we implemented 5 disparate SaaS solutions in 12 months & in doing so, were awarded ‘The Most Innovative Use of HR Technology in Canada’. The following year we’d go on to win Canada’s Best HR Department – Retail & Hospitality, largely on the strength of our technology strategy. Truly humbling honours.

Since that journey ended, I’ve been asked countless times: ‘How did we do it?’ The truth is that it wouldn’t have been possible without an amazing team of HR leaders, support from our Board & Senior Executive team & a great deal of passion, persistence & stubbornness.

Though there were definitely lessons that are worth sharing. Some were introduced proactively as we foresaw challenges. Others we learned through trial & error. 

Either way, the following are lessons you can use in your own HR technology journeys. 

The Importance of Stakeholder Alignment

In the simplest of terms, I view every technology project in 4 phases: concept, pilot, implementation & sustainment. Each requires a unique approach to stakeholder engagement: 

  • At the concept phase, you’re marketing & selling an idea – conveying a sense of urgency around the opportunity & your proposed solution. 
  • In the pilot phase, your stakeholders have bought into your concept. Now they want to see if it translates in practical terms. 
  • At the implementation phase, they believe in your concept & its practical application, though wonder can you bring it to life at scale? 
  • At the sustainment phase, the bulk of the visible activity has concluded. However, you are still working through opportunities that have arisen in your broad-scale implementation. This is a critical juncture where ‘the masses’ are now end users; adoption is far from assured.

These four (4) phases may occur in several weeks, though more likely over several months. Circumstances change in organizations; priorities shift & externalities can throw even the best-planned project off-course.

Solution: Create robust & recurring feedback loops. Be it a Steering Committee, Employee Council, or User Feedback Surveys, involve end users at every phase of your project. Collect their feedback, review it, take action & communicate at every part of your implementation. There hasn’t been a single project I’ve led where upon reflection, I believe we communicated too much. 

Engagement & alignment is essential to sustaining momentum.

The Importance of Project Pilots

Every technology project I’ve ever led had a pilot phase. And I always choose the most challenging stakeholders. 

But won’t that increase the likelihood of failure?! Exactly.

If you stack the proverbial deck & select pilot stakeholders you know will succeed, it’s not representative of reality. Great talent will often succeed despite the imperfections in a pilot. That won’t be the case for the majority of your end users. So, if you only choose your best people to pilot your technology, when the time comes to roll out beyond your initial pilot cohort, errors will emerge & you won’t be resourced to adequately address them. They’ll blame poor implementation (you). 

Solution: This may sound counter-intuitive, but you actually want to ‘break’ things in the pilot phase, when there is patience for & acceptance of errors. So choose to pilot with users you know will struggle with adoption. Like it or not, technology projects can become political fodder in organizations. A pilot phase provides you with needed air-cover to make mistakes, provided you socialize this with & gain alignment from the relevant project sponsors upfront. Take advantage of this; you don’t get to be ‘new’ forever.

Secondly, in the pilot phase, you have a project team dedicated to a smaller scope & scale of implementation. Opportunities will be caught & resolved much earlier. You have the resources to support the most-challenged stakeholders; the individuals who need the greatest support. This often isn’t possible with a systems-wide implementation, when communication & training is scaled (generic) & resources are stretched.

The Importance of Mindshare

As mentioned earlier, circumstances change in organizations; priorities shift & externalities can throw even the best-planned project off-course.

When a technology project loses the organization’s attention & focus, it can quickly wither & die; starved by the lack of momentum necessary to sustain it. In most organizations, the stated priorities of senior leadership determine the mandate. We align resources to the items in the same manner. 

Running a technology implementation project can feel like you’re building the plane while you’re flying it. That’s because stakeholders can only dedicate so much time to new initiatives when the core business still demands the majority of their attention. To address this, some organizations set up Project Management Offices (PMOs); essentially project air-traffic controllers tasked with ensuring that there aren’t too many initiatives occurring in the organization at once. They also ensure that projects don’t collide with known, recurring activities. Though even in organizations where this added layer of project planning is present, there’s perpetual jockeying for the time to implement new initiatives. In essence they’re all competing for mindshare. 

Solution: Negotiating an appropriate timeline for your technology is critical to ensure it receives adequate attention from stakeholders. This must occur at the most senior levels of the organization, as commitments made at middle management layers are conditional at best. In the concept phase of your project, ensure senior leadership is aware & aligned wth the project timing & timelines. They must be clear on what time you need to be effective & how they will need to support it.


The aforementioned tactics are three that I thought were worth sharing? What do you think? Have I got it right, or have I missed the mark? Leave your comments below. Please also include any other tactics so that others may benefit from your knowledge & expertise.

Use a Flashlight, Not a Hammer: Converting Analytics into Actions

HR professionals have a complicated relationship with data.

In an earlier article, I referenced my own experiences with HR data dating back 15 years. At that time, data was the ‘it’ topic in HR. The thought leaders of the day believed HR data, in tandem with qualitative inputs (a functional specialty), would sell organizations on a more ‘human’ path forward. When we arrived at the destination, HR would be well-positioned as true strategic partners.

Except in a lot of organizations, not much changed.

Instead, HR, though now armed with an overwhelming volume of data, was tasked only with creating scorecards & distributing reports. Rather than take on a strategic mandate, too many HR departments instead dutifully reconciled headcount, tracked training completion & reported on employee turnover.

Our future proved nothing more than a dream. Our reality was unchanged.

HR Data as a Hammer

Before long, others began to ‘quantify’ HR, in a lot of cases leveraging the very HR data we had been tracking. A myriad of vendors consultants developed assessments, leadership reviews & surveys to quantify everything from happiness, trust & commitment, to name but a few.

Absent of HR influence (or sometimes in spite of it) a lot of these programs when introduced into organizations became pass/fail. We kept score & developed rankings; there were clear winners & losers. Poor performances often came with consequences.

In far too many meetings, there was accountability, though no coaching. Another unintended result? Under pressure to perform, we started to see the worst in people.

Unfortunately I’ve led a few investigations where a business leader manipulated HR data to achieve a more favourable result. In one case, a leader completed dozens of fraudulent employee surveys to inflate their overall worksite engagement score. In another, a leader bribed their employees with promises of salary increases in exchange for more favourable feedback about their leadership.

Why? In both cases the result became more important than what it signified.

I’ve seen this repeatedly over my career in many contexts. When discipline enters into the equation, behaviour changes. People become guarded, suspicious & in some cases develop unhealthy fixations with a result.

A poor result becomes an unbearable risk. Errors in judgment follow.

Most HR professionals joined (or chose to remain in) the HR profession out of a desire to enable people. Though in organizations where HR data is an impetus for corrective action, partners become adversaries. It’s hard to build trust with a function who can, based on a single poor metric result, be tasked with supporting your corrective action.

More broadly, in cases where organizational trust is lacking, you will spend your limited time debating the recency, accuracy & legitimacy of the data. You will waste time, stress relationships & ratchet up political maneuvering.

You won’t be discussing (or solving for) root cause issues.

Data Without Context Has Little Value

It’s true that data, viewed as an indicator, can reveal opportunities that require your attention as a leader. Those that have worked with me know I love analogies. I have often likened solving problems in business to trying to find a needle in a haystack.

Data (alone) doesn’t pinpoint the needle; it reduces the size of the haystack.

To lean on a singular data point to assess performance is an unfair simplification in nearly every scenario. Turnover, for example, is subject not only to multiple controllable variables within the four-walls of an organization, but also multiple factors (economic, regulatory, etc.) that are outside the control of a single organization, let alone a single individual.

Data requires context. The most effective method I’ve found in establishing context – a conversation. Enter the HR professional.

It’s 2018 & we again have a golden opportunity to leverage HR data as a profession.

Not in its tracking or its reporting. In its application.

If your organization’s intention & that of its leaders, is truly to improve performance & not simply to punish, remove the disciplinary implications from your HR data.

Instead use HR data as a starting point. As an opportunity to add context & understand both the local & broader organizational influences. When the potential for discipline is removed from consideration, stakeholders become less-defensive & more collaborative. Rather than engage in protracted, petty, political back-and-forths, they will reach out for help & partner with you to identify & solve the problem(s).

The stakeholder brings the on-the-ground context. The HR professional brings data & the expertise to blend the qualitative & quantitative. Together you’ll solve the problem.

What was once adversarial, becomes mutually-beneficial.

If accountability is an important part of your organization’s culture, you can still include it under very specific circumstances. I’m an advocate for corrective action in cases of poor integrity (as listed above) & when there is no partnership in creating / implementing an action plan. We don’t punish you for a result; we hold you accountable for taking action(s) to achieve the solution.

The key lies in context & in creating an environment where opportunities are quickly identified, openly discussed & ultimately solved in partnership with stakeholders.

HR professionals – it’s time to take back our data & use it to illuminate, not punish.