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TH1Q&A
Setting team goals that inspire effort without inviting failure is one of the hardest challenges leaders face. This article gathers practical advice from experienced leaders who have learned to strike that balance in their own organizations. Their strategies range from establishing confidence thresholds to giving team members control over the variables that drive success.
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Rick ElmoreCEO, Simply NotedThe rule I go by: a stretch goal has to feel achievable to the person doing the work, not just to me. I've set targets at Simply Noted that looked fine on a spreadsheet and then watched the team quietly disengage because the number felt handed down rather than built with them.
The lesson came early. I set an aggressive production target for our note-writing team without asking anyone closest to the work whether it was realistic. We missed it, trust dipped, and I had to rebuild credibility before the next cycle. Now I set the outcome and let the team set the pace, then I check in on whether the milestone still feels earnable, not just theoretically possible.
One habit that helps: I ask people to tell me the goal back in their own words before we commit to it. If they hedge or go quiet, that's the signal the target is too aggressive, and we adjust before it becomes a trust problem instead of after.
Rick Elmore, Founder/CEO, Simply Noted (simplynoted.com)
Tzvi HeberCEO, Ascendant New YorkI follow a general principle when it comes to establishing performance metrics for facility administration at healthcare facilities: quality over quantity. Any stretch goal should never jeopardize the completeness or accuracy of administrative and/or operational workflows. When establishing stretch goals for either processing facility logistical requirements or updating organizational documents, we assess whether an increase in target volumes will result in increased administrative errors. As such, if meeting the desired higher target will compromise the quality of operations, we immediately stop the stretch goal. One of the most important lessons learned during previous cycles is that there is no substitute for accuracy and the inclusion of quality safeguard measures, as excessive pursuit of volume results in decreased levels of employee confidence and increased amounts of administrative rework. Therefore, by prioritizing operational integrity, we ensure that all team members have challenging yet achievable performance goals based on high-quality, long-term execution.
Drawing a distinction between an aspirational objective and one which is unrealistic involves using the 70% confidence threshold. When establishing objectives for the first quarter of each year for our various administrative departments, I have team leaders assess proposed objectives. If there is 100% confidence by the entire team, then the objective is likely to be less aggressive than desired. Conversely, if confidence drops below 70% as a whole with respect to the team's ability to achieve the objective, it will most likely result in loss of credibility among team members, creating undue anxiety. In addition, the optimal "stretch" exists in the middle area (between 70%-80%), where achieving the objective is possible through creativity and problem solving. One of my lessons learned was that when objectives were established at or below the 70% level of confidence, we lost the engagement of our team. Establishing objectives within the defined range of the 70%-80% confidence threshold results in the operational excellence of the team while also demonstrating that leadership values the expertise and professionalism of the team.
The rule I settled on: the target has to be achievable with the team and the time that actually exist, not the team we plan to have. Setting a number that silently assumes a hire nobody has made is the fastest way to make a goal meaningless.
Where I draw the line is at whether the person owning the goal can describe how it gets done. Not guarantee it. Describe a plausible path. If they can, the target is ambitious. If the honest answer is that they would need everything to break their way, it is a wish, and everyone knows it on the day it is set. That is the moment trust is lost, not at the end of the quarter.
The lesson that changed this for me was a period where we set targets deliberately high on the theory that aiming high produces more even when you miss. What it actually produced was people quietly deciding the number was not real and working to their own private target instead. We lost the ability to plan because I no longer knew what anyone actually expected to deliver.
What I do now is set the target at something the team believes, and treat the gap between belief and ambition as a separate conversation about what would have to change to close it. That conversation is useful. Announcing the bigger number and hoping is not.
The signal to watch: if nobody argues with a target, it has not been read carefully.
Sahil KakkarCEO / Founder, RankWatchThe biggest lesson I learned is that teams do not lose trust because a goal is hard. They lose trust when the difficulty was hidden at the start. Now I make the stretch explicit. I state what must go right, what tradeoffs may be needed, and what support will be available. That honesty changes the emotional contract. People can handle pressure when it arrives with clarity.
My practical rule is that a stretch goal should leave room for learning without making failure feel prewritten. If the target is so high that every setback confirms defeat, the team disengages early. I would rather set a goal that sharpens standards and exposes new capacity than one that looks bold in a meeting but weakens belief over the cycle.
David JolesChief Operating Officer, PURCOR Pest SolutionsOne of the most important things to do here is assess your recent targets for the last cycle you just completed. I've always found that a really helpful way to make sure that every goal or target you set is realistic is to see how well similar ones have been completed recently. If you've just finished up a cycle where a particular target was not met, it doesn't make sense to then go into the next cycle with that same target re-adjusted to be even bigger than before. That's not only just not going to work, but it's likely to break trust, because your team will wonder why you've disregarded the fact that they struggled with something and instead asked them to do even more. When it comes to targets that were accomplished, you can then take those and make them slightly bigger in order to have a successful stretch level.
Bharat SharmaDelivery Manager, Enterprise CX Solutions, eSignlyTrust is upheld when leadership indicates the goal yet allows the team to determine the way there. In my history of managing enterprise delivery cycles, the tipping point for the team is rarely about the difficulty of the goal, but rather the lack of free agency and authority to achieve it. When leadership sets a tough goal and a clear process to get there, they are not leading: they are micromanaging risk, which means a lack of faith in the team's operational capabilities.
In order to differentiate achievable challenges from unrealistic ones, I operate by the "lever ownership" rule: if the team does not know what specific process levers to pull in order to meet the goal, the target is unrealistic rather than a stretch. For instance, when I set ambitious goals for optimizing digital document workflow, I outline the business case in terms of speed and compliance, but delivery leads and architects determine the technology and project implementation. As they, in fact, own the awareness of the process, they are more committed to achieving the result.
One of the key realizations when I had to scale delivery processes internationally was that a stretch target cannot be a request for additional manual hours. This is a failure of leadership masked by ambition. Real stretch targets have to rely on innovations, process improvement, or technology use. If the goal can only be achieved through perspiration, it means that you are not building a culture of high performance, but promoting burnout instead.
Sahil AgrawalFounder, Head of Marketing, Qubit CapitalWhen the whole team hits every number in a cycle, I read that as the numbers being set too low. We are about 60 people and fully remote, so misses every quarter look normal here. I want a hit rate somewhere near 60 percent.
What decides the line is who carries the cost of a miss. If a stretch number lands and nobody's pay moves, people will push at it. Attach money to it and they will negotiate the number down before the cycle starts. I guess that is a compensation question more than a goal-setting one.
You can tell within one cycle which kind of team you are running. Our sales lead set a number last quarter he privately told me was not reachable. He missed it by a fifth. Then he set the same number again.
Hasan Can SoygökFounder, RemotifyMy rule is to stretch one variable at a time: volume, speed or scope, never all three without added capacity. Before setting the target, I ask the team which assumption must hold and what evidence supports it. We also define an early warning point that triggers a scope, resource or timing decision. Ambition demands better execution; distrust begins when success requires hidden overtime or perfect conditions.
Mark SturinoVP of Data & Analytics, Good AppleI'm a big believer in collaborative goal setting for situations like these. This approach gives everyone a chance to weigh in and give feedback on their workload, confidence, and pain points. We'll usually set three big-picture, company-wide goals: a "survival" goal, a "success" goal, and a "stretch" goal. Hitting survival means we can maintain operations, staffing levels, and pay. Success means cost of living raises for everyone and some individual performance bonuses. Hitting the stretch goal means a bonus for everyone.
Carolyn VasquezFounder, Ready Rental CleaningI set the target at what my middle teams hit on a normal week, not my fastest crew's best day. That's the rule of thumb now. I used to set targets off the top performer's peak day. The other crews read that as rigged before they even started. A stretch number only moves people if most can picture hitting it with focus, not luck. So I pull the real pace from full weeks in real homes, take the median, set it a notch above. I show the crews the actual pace numbers behind the target, not just the final figure. Speed targets shift every cycle with the season and the crew mix. The room-by-room checklist stays fixed no matter what the pace number does. If a team clears the new number for a few cycles, the target was soft, and it moves again. I moved both the pace and the checklist together once, early on, and the crews stopped trusting either number within a few weeks.
Chirag KulkarniFounder & CEO, TacoThe biggest lesson I carry is that trust breaks faster from arbitrary goals than from hard goals. Teams can handle a steep climb when they understand the logic behind it. They lose faith when the number seems pulled from executive optimism. So my filter is whether I can clearly explain the target using real signals like past conversion behavior, operating capacity, and speed of decision making.
I also ask one uncomfortable question before locking any goal: If we miss this by a small margin after executing well, would I still believe it was the right target? If the honest answer is no, the goal is too aggressive. Good stretch goals should improve performance even when they are not fully met. Bad ones create defensive behavior, sandbagging, and quiet disengagement.
Rajneesh JaswalCo-founder, Cadre ODRA target damages trust when it lands as a number with no reasoning attached. If people can see what has to go right for it to work, they'll usually stretch further than you'd have asked. If they can't see it, they write it off in the first week and you've lost the cycle before it starts.
My rule of thumb is to test the assumptions rather than the ambition. Write down the four or five things the target depends on, then ask how many sit within the team's control. If most of them do, push hard. If the number rests on a regulator moving or a large partner signing, keep the ambition where it is and measure people on the work that leads there instead of the outcome itself.
I'm comfortable taking risks as long as they're calculated ones, and data is what makes them calculated. Aggressive timelines tend to be earned well before they're announced, and teams can tell the difference.
Vincent NeroVP General Manager, SuccessoriesMy rule is that a stretch goal is only fair if I am willing to recognize the effort at the point it falls short. If a team hits 80 percent of something genuinely hard and hears nothing, they learn that ambitious targets are a trap, and next cycle they negotiate for something safe. That is how a company loses the ability to stretch anyone. So we set the recognition trigger at the same time as the target, not after we see the number.
The practical version of that is to break one big stretch into steps that pay along the way. We had a department where the entire reward sat at a 30 percent increase for the year. Nobody in the room believed they would get there, so nobody pushed hard early. We rebuilt it as three markers: a small award at 10 percent, a better one at 20, and the original one at 30. Same target, same budget, three chances to feel like the work counted. They finished at 24 percent, which is well past anything they had done before. This allowed us to come into the next planning cycle asking for a bigger number instead of a smaller one.
The other half is being honest about which kind of goal it is. Some targets are commitments and some are stretches, and blurring the two is what breaks trust fastest. If everything is presented as a must-hit and half of them were never realistic, people stop believing any of it. Say plainly which is which.
The line I draw is this: if I cannot describe a believable path to the number, it is not a stretch goal, it is a wish, and putting a wish on someone's scorecard is a decision to make them feel like they failed.
Ronan LeonardFounder, Intelligent ResourcingI set stretch by matching it to the team's learning speed and level of autonomy. For people who learn quickly and are encouraged to experiment, I set higher stretch and let them choose tools and report what they discover. For those who prefer established responsibilities, I keep targets more concrete and directive. Rule of thumb: only push significantly beyond current scope when the person or team has shown they can learn and adapt quickly; otherwise, keep goals achievable to preserve trust.
A useful stretch goal should make a team more disciplined, not more performative. The strongest indicator is whether people become more precise about inputs, ownership and timing once the target is introduced. When a goal is set too high, conversations often become abstract because specificity would reveal how fragile the plan actually is.
I now look for what economists would call incentive distortion. If the target nudges smart people toward shortcuts, delayed reporting, or polished updates that conceal operational strain, leadership has crossed the line. Ambition earns trust only when the measurement system rewards truth-telling at the same pace it rewards results.
