June 17, 2025
by Stephen T. Messenger
Too many professionals make the same mistake: they wait to be told what to do. If we ever find ourselves asking, “What do you need me to do, boss?” Stop. That question signals hesitation, not leadership.
I once had an incredibly competent, smart, and reliable person working for me. They would receive tasks, knock them out quickly, and fade into the background for a while. Once they became a little bored or had a face-to-face with me, they would default to their go-to phrase of asking what to do next, thinking they were being helpful and supportive.
But they weren’t. This person did not think for themselves and tackle problems until being asked. After realizing the pattern of being unable to identify and solve problems on their own, I counseled them with, “What I really need you to do is: know what to do without asking, and go do it.”
It’s our job to anticipate organizational needs and solve them before the boss even knows. If we want to be indispensable, do four things: read the terrain, understand intent, act early, and accept risk. General John Buford did it at Gettysburg. We can do it at work.
Take the High Ground
In June 1863, Confederate General Robert E. Lee led the Army of Northern Virginia into southern Pennsylvania, searching for a decisive battle on Union soil. As Union forces scrambled to respond, Brigadier General John Buford arrived in Gettysburg on June 30th with his cavalry. He had no specific orders telling him what to do.
But Buford didn’t wait for instructions. He surveyed the landscape and immediately saw what mattered most: the high ground. The ridges west and south of Gettysburg offered the perfect defensive positions, essential for holding back Lee’s advancing army. He also knew that Union reinforcements would be coming from the south, while the Confederate forces would approach from the west.
Without asking for guidance or permission, Buford acted. He pushed his cavalry forward to delay the Confederates, buying time for Union infantry to arrive and prepare defensive positions on the high ground.
His judgment proved decisive. On July 1st, Confederate troops ran into Buford’s screen and were delayed for hours by disciplined Union cavalry. That precious time allowed the main Union force to occupy Cemetery Hill and Culp’s Hill, terrain critical to the Union’s success over the next three days of battle.
Because Buford acted early, read the situation, and accepted the risk of committing his forces without orders, the Union army gained a crucial advantage that shaped the outcome of the entire battle.
Four Ways to Be Proactive
Buford didn’t seek input from his boss or wait for directions. He read the terrain, understood the boss’s intent, acted early, and accepted risk.
Read the Terrain. We need to be the ones who understand what’s happening in more than just our own little world. We must be able to read a room, know what is working and what isn’t, and see where we can help.
We do that by being engaged. If there’s a meeting that may not apply to us, ask to attend. Learn about other departments. Shadow our buddy in another section. Find out how our role affects everything else.
Buford knew how to read the terrain. He assessed where the bad guys were, and good guys were along with how long it would take them to arrive. He saw the high ground as decisive and started thinking about how it would help achieve organizational outcomes.
By being knowledgeable about the big picture, we are an enabler to the boss.
Understand the Boss’s Intent. The military talks about knowing commander’s intent two levels up. It’s important to know what our boss and boss’s boss are trying to achieve. This intent can be thought of as the “why” behind what we’re doing.
If we know “why” the organization needs something to happen, then we can more easily determine “what” to do and “how” to do it in the absence of orders. When we know what the bosses are trying to accomplish, then we can adjust as the situation changes.
Buford did not know Gettysburg was going to be the decisive battle of the Civil War. However, he did know that George Meade’s goals as the Commander of the Army of the Potomac were to stop the Confederate advance above the Mason-Dixon Line and destroy its forces. Buford made decisions from knowing commander’s intent.
We must know organizational goals which allow us to act accordingly in the absence of orders.
Act Early. At the 2025 Army War College graduation, keynote speaker General James Rainey said that colonels always operate from the offense. This charge applies far beyond colonels to proactive employees. They need to know their limits of authority, and act aggressively within those limits.
We all want subordinates who take the initiative, therefore we should be subordinates who take the initiative. Solve problems, execute decisively, and make things happen. The best ones are solving conflict long before the boss even knows about them.
When Buford arrived at Gettysburg, he didn’t wait to receive guidance. He acted early to shape the battlefield by delaying the Confederates and choosing the defensive positions that would last most of the battle. When his boss finally arrived, conditions were already set for success.
It’s our job to make decisions in the absence of guidance, solving problems on the spot.
Accept Risk. It’s easy to ask for permission for everything. That keeps us out of trouble. But it’s not productive to ask every time, and frankly, it’s annoying for the boss. We all have levels of delegated authority and risk that we’re allowed to take. Use every ounce of that!
Remember, it’s only prudent to accept risk on the boss’ behalf when we understand the conditions and know their intent. These two benchmarks are a guide for placing a decisional risk onto our shoulders. We can take risks as long as we’re acting in good faith and understand our limits, while keeping the boss informed.
Buford assumed all the risk by setting conditions for a massive battle on the field of his choosing. Upon arrival, he immediately sent word to his boss over 10 miles away of his actions. When Major General John Reynolds arrived, he reportedly said, “Good ground… the Devil’s to pay.” In other words, “Great call!”
It is our job to understand the situation, read the terrain, understand the boss’s intent, act early, and accept risk while keeping the boss informed.
Here’s What I’ve Already Done
Instead of asking, “What do you want me to do?,” a better way is to tell the boss what we know, how that’s a problem, and the steps we’ve already taken. Most times, the boss is thankful that we took the initiative and worked towards a solution, so they don’t have to.
Don’t ask what needs doing. See it. Do it. Solve problems before our boss even notices they exist. That’s how we become essential.
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