Asking these three questions constantly will help you achieve your goals

“What are your goals?”
“What are your goals?”
Image: Jopwell
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We all understand that setting goals is a good idea. But many struggle to convert their goals into action.

The standard course of action for implementing new ideas is to organize task forces to investigate; share reports of early progress with the executive team, accept feedback, and then break up the team to complete their individual tasks. Those fortunate enough to have open calendars are quick to get gain ground, but others who are not so fortunate are quickly overtaken by the undertow of their departmental disorganization. And although they will still chip away at their tasks, this is the real death of the project. As time drags on, waiting begets impatience and finally, team members lose interest. The longer the project lies still, the less likely anyone will dare disrupt its stagnant surface.

Does that sound familiar? I see it almost everywhere I go. But thankfully, you don’t have to be a Scrum Master or logistical genius to fix this issue. Like a Tour De France athlete riding a single-speed bike, you simply need a better mechanism to make all that peddling worthwhile.

I’d suggest asking three questions, at regular intervals, to build that mechanism.

What are your goals?

Defining specific goals seems like an obvious step—it’s almost painful to write—but it’s unlikely that your team is doing it correctly. Proper goal setting will help team leaders think tangibly about measurable efforts, keep other leaders apprised of how the initiative fits into the organization’s wider goals, and prepare them to assist. This will further hold them accountable to those goals.

When you focus on this question, your team will adjust their daily regimens to be accommodating to their goals. Every email, phone call, meeting, and task in the day will suddenly align with their goals, and, if not, you’ll tell them to table the task for future consideration under a new future goal. Everything your employees do must be tied to their goals or a colleague’s goal. If it doesn’t fit, it doesn’t happen.

This question is especially helpful when colleagues need interdepartmental help. When someone reaches into your department for help on a project, it’s always appropriate to ask, “What goal can I help you accomplish?” This strategy completely changed one business with which I consulted. Its head designer was constantly bogged down with reactionary brochure, image, or design requests from reactionary sales staff. When he began framing all requests within the context of goals, the frequency of requests slowed down considerably, and the designer was better able to anticipate and answer the true needs of the sales department. The marketing department was less stressed, and sales felt listened to and supported.

When will you achieve your goals?

Goals are a great start, but utterly useless if not achieved, and this question is the elegant solution. A ballet recital for your child and your mortgage payment all happen on a schedule, but for too many ongoing projects at work, deadlines don’t actually exist. I hear your objection already: At work we want things done “ASAP.” But because ASAP doesn’t come with a deadline, this “act fast” approach is likely to take even longer. While ASAP to you may be one hour, for a colleague it may be weeks.

Ongoing projects offer no moment in time to actually debrief, breathe, and learn. They just drag on, and things don’t change until there is a glaring problem. This is another reason why specific deadlines are important. Every project from every leader must fail or succeed, and assigning a date makes this a reality.

When failure and success become real, the opportunity for every other executive in your team to learn dramatically increases. Ongoing projects that used to fade from one month to the next deprive us of the opportunity to learn from failure, or learn from success. That means that if a project doesn’t proceed, all time spent was a complete loss. But deadlines utilize all team time as a potential opportunity. Leaders can ask, Why did it fail/succeed? How could the project have gone better? How will we improve next time?

Your team should fail or succeed as one—if an executive on your team fails and colleague could have prevented it, they failed together. And this is why question three is so important.

What can I do to help?

This question fulfills a leader’s support role, but more than that, it sends a concrete strategic message. It communicates that your team is expected to ask you and others for assistance. Anyone operating in a vacuum is prone to error, so we want people under our care to feel free to ask for help in the same way we want them freely offering help to their teams.

Asking how you can help is also a subtle reminder you are trusting your team to accomplish what they say they will and a way to take excuses off the table. Leaders can’t blame circumstance, budget, or time after you’ve asked this question, because these are all things for which they could just ask you. Similarly, if you don’t want teams making excuses, it’s on you to make sure their needs are addressed when they do ask for assistance. If you don’t, then they do have an excuse.  


I know it sounds simple, but there is one last thing you need to know before transforming your culture with these three questions. This strategy will fail if you miss the most important step: Write down the goals and refer to these questions often. If you’d like to track them in project management software, that’s a great step, but it’s important you continually encourage your team and hold them accountable to their own goals.

Teams will miss deadlines and fail spectacularly, but that’s by design. Those moments are critical debrief opportunities and set the expectation that no goal will disappear. Failed goals provide a coaching opportunity and successful goals allow the victor to coach the team. Failure and success become objective metrics and teaching opportunities, whereas before failure was an amorphous void that couldn’t be measured or discussed.

Keeping your team fresh is as simple as repeating the exact same trivia trifecta as often as necessary. What are your goals this quarter? This month? This week? This workday? These questions convert your “are you done yet” conversations into a moment of encouragement and support. They turn nagging into responsibility, and, most of all, they turn excuses into opportunity.

So, I have three final questions. What are you going to implement? When will you get that done? And what can I do to help?