Lead from the Back: Building Alignment Through Trust & Execution

One of my very first jobs was leading summer wilderness tours and canoe trips through Northern Ontario. People would join the trips, at first like a fish out of water, but 20 days later they'd emerge a different person because of what we were able to do as a group.

Those weeks spent bouncing down the Missinaibi River, the white water spraying against my face, shaped the leader I am today. In a canoe, the guide sits in the back, using a bladed paddle to determine the direction of the team, and that’s the role I like to play in business as well. 

I'm a big believer in servant leadership; that the best thing you can do as a team lead is to equip and enable the people you work with and work for. The answers to most complex problems in life and in business are generally solved—or at least better addressed—by surrounding yourself with amazing people. 

But having the right people around you is only one ingredient. The trick is to put the right pieces in place so that each person is not only going to be successful in their role, but also totally understand how it aligns to the bigger picture. It's so critical to success. 

Without a common vision of direction and cohesive, defined processes to guide a team toward the end goal, it’s easy to veer off course. The most effective teams develop a culture of relentless focus and execution and put into place operating systems to drive alignment and accountability. I witnessed firsthand just how powerful this approach can be while working as a Senior Consultant at Deloitte.

Unlocking the Secret to Potential

At Deloitte, I had the pleasure of working on the Managerial Design Team. From law firms to banks to government organizations, I consulted with a wide array of businesses and saw firsthand the ingredients, the culture, and the processes required to create highly effective teams. It was also during this tenure that I was smitten with tech. 

The level of innovation, experimentation, openness, and ability to take risks in tech companies was unparalleled compared to others in other industries. They have this amazing ability to create conditions for their work to be realized, and the space employees had in these types of companies to make their own decisions, to have a real impact on the business, was astounding. 

That environment was what I had been looking for since my days as a wilderness guide. I knew that if a leader can unlock the potential of each member of the team, truly amazing things can happen. 

Trust Requires Horizontal and Vertical Alignment 

Another priceless lesson I learned as a management consultant is that trust is only effective within the walls of alignment. Hiring great people, and then just saying, "Go work on what you want," is actually disorienting. How can you really trust this person when they don't even know what they should be prioritizing in the context of the business? 

Each person, regardless of where they are in the organization, needs to understand their role and the vision for team vision, and then have the freedom to find new ways to solve problems. This type of alignment—vertical alignment—gives people complete understanding of their role and the vision for the team so they can excel and find new ways to solve interesting problems. 

By creating alignment across teams within an organization, that is, knowing who is working on what project and why, they can focus better, creating more efficiencies and reducing redundancies. This is called horizontal alignment, and it can help teams eliminate overlaps and reduce gaps.

And if you establish alignment both horizontally and vertically throughout an organization, you give people the ingredients required for trust because they know the direction the company should be going. They know that they have space to experiment, and they understand the outputs they’re driving to.

A Finishing School in Focus

This understanding of alignment truly calcified when I left Deloitte and experienced it from the inside as the Chief of Staff at Influitive. My role was to help the company stay focused on the most important tasks, develop and cascade the strategy of the organization, and ensure that the most important strategic initiatives were being executed.

This role clicked really, really well with me because I'm methodical and I like to understand how new ideas fit into what we're doing. Plus, I had the enormous benefit of working with a thoroughbred, successful CEO, Mark Organ. Mark had created a set of goals for himself that were almost superhuman: build a billion-dollar company, create a trillion dollars of wealth for anyone who's worked with him, raise $40 million in financing, enter four markets, and join three boards. 

As soon as I joined, we began a hiring blitz with the goal of doubling our revenue and our team size in a year. This was a massive undertaking, and if we weren't aligned and focused as a team, everything would have fallen apart. 

That exercise gave me a new sense of appreciation for building in the right processes and operations within the team and instilled in me the importance of focus for any organization, but more so for those in growth mode. It also gave me the opportunity to show Mark the leadership skills I had been building throughout my career. Within my dedication to alignment and execution, Mark saw an opportunity. 

Influitive had been building a new business line, Upshot, and now that it had gone from idea to MVP, its success was going to be contingent on growing a team that combined individual, complementary strengths into a cohesive, aligned unit. He asked me to lead that charge. The Chief of Staff role was my finishing school, and Upshot was going to be where I could put those ideas into practice. 

Learning from the Masters of Effectiveness and Accountability

During my time at Deloitte, I had the pleasure of meeting The Emerson Suite co-creators, Doug Emerson and Allison Christilaw. They sold their company to Deloitte in 2011, and I worked alongside these masters of organizational effectiveness, team effectiveness, and cascading accountability. 

Now at Upshot, I was taking the learnings from Doug and Allison and hacking together a system to implement their guiding leadership principles. I bought a goal management software and tried to weave in The Emerson Suite ideas, but it just wasn’t working. It was like using a FitBit: It could show us where we were improving or not improving on a given week, but didn’t bring teams together in a way that sparked the right types of conversation. 

After weeks of creating my own templates and trying to jimmy-rig tools that weren’t really built for team effectiveness, I learned that Doug and Allison had turned their leadership system into an online platform that I could actually use with my team. I was instantly sold.  

Now, The Emerson Suite enables us to get new members of our team ramped up quickly because we have a built-in process in our management. Plus, our remote team members have equal footing with the rest of their coworkers because they're active in team conversations. With full visibility into what each person is working on, I can ensure no one ever gets lost in the shuffle, no matter if they’re in the office or halfway around the world. 

Building Horizontal and Vertical Alignment

The power of The Emerson Suite for me is two-fold: within our team and outside our team. Within our team, using the Weekly Top 5 dashboard is a great way to identify and execute weekly priorities. I can easily view and analyze our weekly focus, how it relates our overall goals this quarter, and even how it relates to the quintessential success factors of one person's role with the team's projects. It's tightly connected in respect to turning our strategy into measurable results. It helps us build horizontal alignment and identify those critical connections as we prioritize strategies.

Outside of our team, I use The Emerson Suite to update the executive team on our priorities. I meet with our CEO every week and we talk about high-level strategy and our KPIs. I also send him and everyone on our executive team our Weekly Top 5 priorities. I open that up to any questions that people have. I ask if any priority looks off or if there is anything they want to dig into. This way, everyone in the organization understands our strategy and how it cascades into tactical priorities. 

This upwards vertical alignment is extremely difficult to achieve. To be able to get our team's priorities on our CEO and entire executive team's map is amazing. That's the difference between just putting it in some document that's not connected to any of our strategy, that can't be easily distributed and disseminated in a way that's effective, and having a platform built specifically for this use. 

The Magic of Conversations

Creating an effective, structured work environment is all about driving powerful conversations within my team in a way that can be captured, documented, and cascaded to teams around, above, and below us.

When Laszlo Bock was at Google, he conducted a study that found the most effective teams rely on a high degree of psychological safety, meaning they are able to bring out the best ideas because the team feels they can raise opinions, ideas, and suggestions. They do so without risk of being punished or ignored, and those ideas actually have a real chance of being heard and implemented. 

The most important asset on your team is your smart, diverse, interesting people. Companies or teams that are purely directive driven don't bring people together and will not be the most effective. Conversations are where the great stuff happens. It happens in the mess. It happens in the unknown. It happens in the half-baked ideas that the team feels encouraged to bring to the forefront. If it's just a matter of following orders, you lose out on the magic. You lose out on the best part of a team. 

Keeping track and managing all those moving pieces and ideas makes all the difference when you stay focused. It’s why we could never just use something like a shared Google Doc to try to align our team here at Upshot. It’s not connected to our strategy and can't be easily and effectively disseminated to the team. 

There’s No Blueprint for Success

Startup executives don't have a blueprint for success. Most of what you're doing has never been done before, and you're scaling at a pace that is unheard of in many cases. You can try and skip the foundational work for a certain period of time, but it catches up to you. 

A culture of engagement through focus and relentless execution is what separates startups that succeed from those that fail, and a big part of executing properly is having the foundational tools in place to facilitate alignment. A great management operating system complements the magic of your ideas, the nuance of your strategies, and helps align your vision across all teams.

My advice for any leader who wants to break through the chaos and achieve complete organizational alignment: make visibility a two-way street. When everyone knows the path and has the tools—and freedom—to succeed, all you’ll need to do is lead from the back.