From the Battlefield to the Boardroom, Leadership from 4-Star General (RET) Richard D. Clarke

Over Communicate.

Leaders must continuously reiterate their organization’s vision, mission, priorities and goals. Providing direction once isn’t enough. Be explicit about how you want to receive information and communicate your expectations over and over and over again. And if something isn’t working the way you think it should, recognize you may be the problem.

Lessons from the field: In 2003, I was serving as Commander of the 3rd Battalion, 504th Infantry, 82d Airborne Division, where I was in charge of about 800 paratroopers, five subordinate company commanders and a staff of about 50 people. After a nine month deployment in Afghanistan, about 20% of the unit and an even higher percentage of the unit’s leadership had rotated out, which is common practice post-deployment. Abruptly after that rotation, deadlines (called ‘suspenses’ in the military) were not being met, the unit’s training was not up to standard, incidents of ill-behavior were up and I was not getting the level of information or feedback from subordinates that I had come to expect.

After wrestling with some frustration due to these challenges, I came to realize that I was a large part of the problem. ***As a leader, I needed to actively communicate and then reinforce my expectations and standards to a group of largely new faces. *** So, I started meeting with my direct reports daily at 6am, before physical training, to align on daily priorities. Once we developed this cadence or as I called it, battle rhythm, my expectations became clear and everyone in the unit — from leadership to direct reports — performed at the level that was expected.

Engage At Every Level.

Get out from behind your desk and engage, whether it’s with a fellow leader or an entry-level worker. Ask about their mission, resourcing and morale to identify and fix problems before they become too large or costly to address. Use unscheduled and independent check-ins to your benefit as they elicit the most authentic and useful feedback. Remember, team members will model your behavior — so if you’re engaged, they will be too.

Lessons from the field: In my time as Commander, I frequently traveled to Afghanistan to see how our special operations unit was supporting the war effort — visiting the remote bases, talking with the Afghan Commanders and attending meetings at the Embassy and with the Commander in Charge of the U.S. and NATO missions.

While my days were jam-packed, I found I did my best work at night after my staff had gone to bed and there was nothing left on my schedule. I would poke my head in at various headquarters and Joint Operations Centers to say hello and see what they were doing. Without a set briefing, agenda or entourage with me, I was able to interact more authentically and honestly with people I didn’t work with often — including Soldiers, Sailors, Marines and Airmen, usually several echelons lower. It was exceedingly helpful, but also a lot of fun!

Seek Out Input & Feedback.

The best way to make a decision as a leader is to first, determine what kind of decision you're faced with: If it’s time-restrained, get the facts and make a quick call; If it’s clear-cut, delegate it; If it’s complicated, seek guidance from key stakeholders. Especially on tough decisions around people (hiring/firing), resourcing or strategy, ask for input from all levels before sharing your own opinion. This can help get an honest read from others and avoid the inescapable tendency to agree with the boss.

Lessons from the field: As Commander of the U.S. Special Operations Command, I was in a meeting to discuss resource allocation, specifically whether to continue some very specific programs to the tune of millions of dollars. I started the meeting by sharing my direct opinion on a specific program that I believed needed to be cut. Since I was the highest ranking person in the room and everyone else was a direct report, 100% agreed with my opinion without additional dialogue. Because I’d set that expectation on the first topic, I engendered no conversation and got zero feedback and the staff looked to my opinion on the remaining programs without much question or push-back. If I had sought input first before sharing my own opinion, I could have inspired a deeper discussion that could have led to a more optimal outcome. I quickly adjusted all key decision meetings to ensure that I spoke last after gathering input from subordinates.

Delegate Deliberately and Organize Consistently.

As your organization grows, delegate strategically to preserve necessary white space on your calendar for big-picture thinking and spontaneous engagement. Avoid ambiguity by creating weekly, monthly and quarterly “battle rhythms” that serve as predictable touchpoints for teams to align on the evolving needs of your organization.

Lessons from the field: As the SOCOM commander leading 75,000 people, my main responsibilities were keeping the organization moving and determining where to place future bets in acquisition, resources and strategy. Delegating tasks had become a critical necessity to make room for the open slots on my calendar that I needed for strategic, big-picture thinking. I’d learned if something had to be done, and I didn’t have to do it myself, I should delegate it to someone else.

During this time when I was primarily focused on large-scale decisions, it would’ve been easy to lose sight of individual needs. To avoid that pitfall, I scheduled weekly, monthly and quarterly touchpoints with my direct reports as well as quarterly in-person conferences for all subordinate commanders — the head of Air Force special ops, head of Navy special ops, and so on. We called these face-to-face quarterly meetings the Commanders’ Decision Roundtable where the goal was to hash out budgets and resourcing while facilitating strategic conversations about the key issues for the command. For instance, coming out of the decades-long war on terrorism, where we relied heavily on unmanned aerial systems to collect intel, we needed to shift resources so we could maintain the counter-terrorism mission while prioritizing the new mission: countering growing threats from China and Russia. As you can imagine, the intricacy of these high stakes decisions led to complex, in-person discussions where ambiguity is a lot easier to avoid.

Key Takeaways

In the early stages when an organization is small and scrappy, your job is mainly to execute, but your focus as a leader changes as the organization evolves. To scale strategically and successfully, articulate and repeat your expectations, generate interdepartmental dialogue through spontaneous engagement, delegate, work deliberately and make space for subordinates to share their input and ideas.

Whether leading in the battlefield or the boardroom, stressful situations serve as the best barometer. Intense, high-pressure moments will inspire innovation in well-led organizations and failure in poorly-led ones. In the military, we often say leaders of the future are developed during war-time because there’s no better proving ground than combat. It’s a metaphor that can also apply to startup leaders — the early stages of building a company will be undoubtedly challenging, but the best will come out of it stronger and primed to scale.