The Obstacles that Stop Smart Teams from Setting Goals—and How to Overcome Them

Dart board with dart in bullseye — Business goal setting obstacles

Goals are one of the evidence-based ways to optimize how your team works. Implementing an effective goal execution system can lead to significant gains in progress—some estimates suggest as much as an extra workday each week

An effective goal execution system has three components: 

  1. Setting productive goals

  2. Creating a plan to achieve those goals

  3. Developing the habits needed to execute

Setting productive goals is only the first component of the goal execution process—but it’s key. If you don’t set productive goals, the planning and execution phases are set up for failure and you won’t reap the benefits that goals can offer.


In this article, we describe some of the obstacles that cause high-performance teams to fail to set productive goals in the first place. Then we’ll address each of them and provide some advice for overcoming the obstacles. 


We cover:

One of the biggest reasons teams don’t consistently set goals is that they don’t understand the massive benefits that written goals can confer to teams. 

Because they don’t understand the benefits, setting goals may not seem like a good use of time.


“Why don’t we just do the work instead of struggling to articulate exactly where we want to end up and how to measure our progress?”


Response: The reason is that it’s less effective. Explicit goals have an enormous ROI. One analysis suggests that setting specific, challenging goals leads to an 18% increase in the value of output over “do your best” goals. That’s the equivalent of gaining an extra workday each week. 


Those gains can have real impacts for the company, including a combination of:

  • Accomplishing key projects faster

  • Reducing the need to hire new employees

  • Teams feeling happier and less stressed

The benefits of goals on both progress and your team’s well-being are well documented. 


Read more: What Science Says About How Goal Setting Impacts Company Success

Some teams don’t set goals because they feel too busy. They’re already pushing themselves hard, fighting fires, and working on projects that deliver immediate value. 


They recognize that it’s useful to set goals, but they can’t spare time to set them right now. It’s hard to let fires burn while you’re making plans for the future. The current work is urgent; goals aren’t.


“Why would we take away time from urgent projects and put it towards activities that can wait? We can set goals later, maybe next quarter, when things settle down.”


Response: It’s reasonable to prioritize urgent work over strategic work. If there really is a devastating fire burning, then you should spend your time putting it out. 


But ask yourself—what if I let this fire burn? Is it as urgent as I believe? Sure, you need to make sure the ship doesn’t sink. But the direction it’s sailing is also very important.


And let us assure you: it’s not going to be easier next quarter. 


You will always be busy. You will always feel like there isn’t enough time to do important but not urgent work. 


The truth is that as little as 2 hours per week of deep, strategic work will make a huge impact. It’s almost always the case that the company won’t collapse if you put that time into setting goals.


Setting goals is like saving money. If you want until the end of the month, you may find that you’ve spent it all and have little left to save. But if you pay yourself first, you’ll find that you can both save and have enough for your other tasks. 


It’s the same with time. If you wait for when you have free time, it will rarely feel like you have time for strategic work or planning. 


But if you make it one of the “big rocks” you schedule time for at the beginning of the month, you’ll find that the urgent things will also still get done.

Another common reason leadership teams of growing companies fail to set goals is that it feels futile. It seems like everything changes so quickly that it's a waste of time to nail down future objectives. Goals can become obsolete as soon as you make them. 


“Why set goals if they’ll quickly become irrelevant?”


Response: The value of goals is that they provide motivation and direct your energy towards things that matter—and away from things that don’t. They help your team work more effectively. 


When the context changes and you need to pivot, your goals can change too. At HabitStack, we advocate reflecting on your goals regularly. That allows you to quickly shift your goals when necessary. 


Shifting goals is useful. It prompts your team to re-evaluate priorities. There are more things we could do than we ever will. Being forced to make goals helps us prioritize and decide what really matters.


"Plans are useless, but planning is indispensable." — President Dwight Eisenhower


Be quick to correct goals as things change, but slow to give up on goals when they turn out to be difficult to achieve.

Some teams hesitate to set goals because they feel oppressive


Both growing startups and established companies need to stay agile. Leaders want to be able to respond creatively to opportunities—they want to be able to change directions easily. 


Those leaders may see goals as an obstacle to changing direction. 


“Won’t rigid goals keep us from adapting and evolving our business?”


Response: The answer is the same as above: Of course you should adapt and evolve your business when necessary. Be quick to correct goals when your priorities shift, but be hesitant to give up on goals just because they’re hard.


And consider the benefit of a little structure: it can bring freedom. Having all your options open at all times can be stressful. You can eat up your time making decisions about where to take your business rather than actually doing the work to get there. 


Goals don’t stop you from staying agile, and they keep you from spinning your wheels. 

Some teams do not set goals because they want to avoid the discomfort of failing.


It feels bad to recognize that you missed a goal. It can be demoralizing and can challenge your sense of self-efficacy


Reviewing goals as a team can also cause discomfort. We fear that we’ll look bad to our peers when we miss a goal. We don’t want to lose face. And what if others miss their goals? Trying to keep others accountable feels awkward.


Response: First, holding ourselves and others accountable is a skill that you can develop—you can learn how to hold others accountable and for what.


For example, in another article on team expectations, we argue that while you usually shouldn’t hold your colleagues accountable for success or failure on things outside of their control, you can hold them accountable for putting in the effort, honestly accounting for what they did well and mistakes they made, and carrying that learning to the next goal. 


When you learn how to create systems for constructive accountability, you can foster better results while maintaining a positive team culture.


Second, we should feel a bit bad when we don’t do what we say we will. That sense of discomfort from letting down yourself or your team can actually be a good thing. It can increase your commitment and help you actually work smarter next time.


At the same time, it shouldn’t be demoralizing. It’s important to recognize that you’re not going to always achieve all of your goals. That’s okay. Maybe your goals are too hard, or maybe there are external factors that are too strong. Beating yourself up for failures won’t help. 


Try to strike a balance between feeling disappointed (and motivated to do better), but not feeling demoralized.

The to-do list is never-ending. There are a massive number of tasks, and all of them are important. How do you filter them? What framework can you use to decide? It feels impossible to weigh them all and come up with the right goals. 


Especially when there are so many different perspectives. Each team member seems to have different ideas about what things matter the most. Setting concrete goals would require getting consensus, and that feels hard to achieve.


Response: Goals are particularly important for teams with endless to-do lists. It's when there is no clear path forward that goals can do their magic. 


It’s true that it’s not always easy to find alignment with your team on what really matters, but, in our experience, virtually all teams can do it. 


You can use an existing framework to help you—for example, Roger Martin’s Playing to Win outlines the approach we favour at HabitStack. 


But sometimes, in the words of Michael Lopp, “You just need to decide.


If you are really struggling to pull out the tasks that are the highest priority, consider engaging with a Business Leadership Coach. Coaches can guide you towards the skills you need to effectively facilitate a prioritization exercise with your team.

Finally, some teams don’t set productive goals because they don’t really know how


They think about what they want to accomplish, but they don’t write it down. Or, they write it down, but it remains vague rather than specific. Or, they fail to specify how they’ll measure progress. Or, they make their goal easy, and miss out on the potential for more transformative gains.


It can be difficult to know not just how to set goals, but who to involve. Can you make them alone, or does your team need to participate? Can you assign goals to your team?


“How do I choose priorities from my massive list of potential work and set goals that actually help us do our best work?”


Response: You need to learn how to set productive goals. At HabitStack, we use “productive” to refer to goals that really work—goals that are effective and provide real benefits. 


“Productive” goals have three characteristics:

  • They are specific. That means that they are constructed in such a way that you know exactly what success looks like.

  • They are measurable. You can keep track of your progress towards them. 

  • They are difficult. Challenging goals lead to better results than easy goals. Productive goals should be hard—but not impossible. 

Try to set your goals so they have all three of those characteristics. 


Also, work on your goals as a team. This gets back to accountability—working on your goals as a group helps keep everyone on track. It also ensures that you’re working in sync towards your long-term vision.

Setting productive goals is the essential first step to developing a system that maximizes strategic progress. And it’s worth developing a robust goal execution system—such a system can lead to massive gains in effectiveness. 


It’s not easy to develop an effective goal execution system, but it’s not rocket science either. These are the essential components. 

  1. Set productive goals. Put aside time to develop a set of goals that are specific, measurable, and challenging.

  2. Make a goal plan. Layout a plan to take you from the current situation to your goal. That means breaking your larger yearly goals up into quarterly, monthly, and weekly goals.

  3. Implement high-performance execution habits. Reflect on your progress regularly together with your team. Keep each other accountable and on track.

Do those things, and you’ll be setting your goals—and executing on them—in a way that significantly increases your chances of success.

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