Good Leaders Use Great Questions to Set Extraordinary Goals

March 12, 2018 Alex Shootman

By: Alex Shootman

  • How do you engage your team in setting extraordinary goals?
  • What would that goal-setting discussion look like?
  • And what’s the real difference between clear goals, stretch goals, extraordinary goals, and pipe-dreams?

Alcibiades (Athenian commander in the First Peloponnesian War) is rumored to have said, “If I command you, ‘Pick up that bowl,’ and set a sword-point at your back, you will obey but no part will own the action.  You will exculpate yourself, accounting, ‘He made me do it—I had no choice.’  But if I only suggest and you comply, then you must own your own compliance and, owning it, stand by it.”

We’ve all experienced it.  When we are told what to do there is a little piece inside of us that resists.  Yet when we own an idea, we will go to great lengths to defend it.  This defiance/defense phenomenon is ingrained in us early; as my eldest son Will (now 21) would say when he was a toddler, “I do it by Will!

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If you are in a business that is expecting great things and is filled with strong-willed people, congratulations!  There is no greater place to be, but you are going to need to turn the conventional wisdom about leadership upside down to drive your business toward exceptional results.

Your first step is to give up chasing the heroic ideal of leadership that’s so ingrained in popular culture.  We’ve all seen movies or TV shows where a charismatic leader takes charge at a decisive moment and tells an embattled band of comrades a list of specific things to achieve.

The leader might be cast as a soldier, a reluctant hero, maybe an idealistic lawyer, a scientist, or a teacher. But they alone decide the course of action; they take the first and boldest steps of the journey; their rhetoric soars towards high ideals.

But they are a leader in a crisis and while shouting ‘Run!’ when a bear crashes out of the forest is appropriate, most of us do not operate in a perpetual bear chasing mode.  It might feel good to try and be that heroic leader, but best to put down the light saber. 

Your people don’t always want to look up for answers. Ambitious, able, and knowledgeable about their field of expertise, they want to be heard.

Good ideas exist at every pay grade.

If step one is to put your heroic leadership instincts to one side until a time of crisis, then step two is about engaging your team in setting the right type of goals.

A mentor, Art Wilson, shared with me the art of good goal setting.  It is about the mastery of four goal types. 

Four Types of Goals

There are four types of goals we can set in any organization:

  1. Clear one the team has high confidence in achieving by working the way they work today.
  2. Stretch – the team is a little less sure of this one, it pushes them but they plan on achieving it the way they work today.
  3. Extraordinary a goal you and others really desire; it is at the edge of your headlights, it is audacious and it will require you to change the way you are working today.
  4. Pipe dreams  a goal that is so far away from reality, no one believes it.  The pipe dream is mere fantasy, it is unattainable and it demotivates the team.

The secret is that if you’re striving toward an extraordinary goal, chances are you’ll hit clear and stretch goals along the way. Even if you fall short of the final extraordinary objective, you’ll have made significant progress—progress that goes beyond what most businesses would expect.

Defining Extraordinary Goals

Now, for all of us Alcibiades wannabes it is time to transfer ownership of our goals.  Let’s imagine a conversation between a leader and a team.

What do you think we can achieve next quarter?” asks the leader.

A team member defines what they think the team can comfortably achieve at the existing run rate of activity and with existing resources.

So, if we pushed harder with what we’ve got, what does that outcome look like next quarter?” asks the leader.

Another team member starts to define a stretch goal.

What do we really want to happen?  What would be an amazing outcome, one in which everything went as well as it possibly could, where do you think we would end up?

The team members start to define what an extraordinary goal looks like.

But, of course, boss, to do that, we’d need x resources, y expertise, and z experience in the team,” they say.

No need for rousing speeches. Yes, you can leave that copy of Shakespeare’s Henry V or the collected speeches of Abe Lincoln on the shelf. Save the heroic words for another day. This simple question-and-answer dialogue has given you a definition of what good, great, and extraordinary outcomes look like—plus an indication of resourcing requirements.

You’ve also got a barometer reading of the mood, aspirations, and concerns of the team. You understand them a little better. And they will see you as a leader who is interested in what they think and what their talents can achieve. If they seem to be lacking in energy and morale, you can start to see what the root of the problems might be.

But, crucially, you can now start to break down the steps and resources needed to achieve the extraordinary goal they’ve described. Specific tasks, timelines, and milestones can be defined, documented, and shared.

This isn’t a pipe dream. The team, based on what they believe they can achieve, has set the goal and tangible steps to achieve it. You’re not persuading them; they’re persuading you.

Vision ≠ Goal

Now you’ll say there’s a flaw in the logic. Leaders set strategic direction, right? How can staff define extraordinary goals when they don’t know the full picture of what’s happening in a business?

First, there’s a crucial distinction between the company’s vision and its operational goals day-to-day, quarter-to-quarter.

Goals are about what needs to be done, by whom, when, and how. The vision answers the question “why?”

Your job as a leader is to answer that final question—establishing the purpose and assigning meaning to activity throughout the business. That’s where you can be aspirational, inspirational, and even heroic, as long as you’re defining and clearly articulating why all of this matters and the point of the journey you’re all on.

Second, if your team doesn’t know the wider operational picture of the business, you have another problem to solve.

You need better internal communication and cross-team sharing of information. And that starts with you. Say more, say it often, and don’t feel that you always need to be the hero. Being clear and consultative (and decisive when needed) is how the best leaders help teams win.

So, here’s your new leadership challenge. Stop trying to persuade people to hit an extraordinary target—and let them tell you how they’ll do it. 

Choose an area where you want the business to excel. Now play out the goal-setting dialogue with your team. The more you do it, the better you'll be at it. And if falling short means hitting a stretch goal, you have nothing to lose and everything to gain.

See our post "What Qualities Make a Good Project Manager?" to learn more about honing your leadership skills.

About the Author

Alex Shootman

As President and CEO of Workfront, Alex drives the overall strategy, vision, and execution for the company, ensuring that Workfront is a dedicated partner in helping its customers transform the work experience. Shootman brings more than 25 years of experience in all areas of revenue and profit generation for technology organizations, with significant experience leading SaaS-based companies. In his free time Alex can usually be found trying to convince his legs that they really don’t hurt on a road bike or running trail, admiring the view from a 14er in Colorado, or down on a reef in his home state of Hawaii. That is if his four kids leave him any free time.

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