How leaders can avoid the dangers of 'yes' people

If 'yes' is all you're hearing, you have reason for concern.
How leaders can avoid the dangers of 'yes' people

Leaders who surround themselves with an ocean of nodding acquiescence are liable to run into icebergs. In order to discover issues while they're still small and encourage team members at all levels to propose creative solutions and challenge ingrained ideas, leaders should navigate their teams towards a culture of candour and away from blind agreement.

"The danger of surrounding yourself with 'yes' people is that often those people are telling you what they think you want to hear versus what they actually think," said Kim Scott, author of Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity, based in the US's San Francisco Bay Area. "If you haven't created a culture of psychological safety on your team, chances are people aren't going to feel empowered to challenge you when you're wrong, which can lead to disastrous consequences."

Joselin Martin, CPA, CGMA, owner of True North CFO, based in Baltimore in the US, has witnessed both the consequences of stifling candour and the benefits of maintaining frank communication in all types of business relationships, whether it's between owners and financial managers, managers and direct reports, or finance professionals and clients.

Martin was working as a financial manager for a construction company during the years leading up to the 2008 Great Recession, and she could see from her projections that the organisation was highly susceptible to any changes in the industry. She believes that her ability to have uncomfortable conversations with the general manager about challenges facing the organisation allowed them to make hard decisions that helped avoid the worst of the crisis.

"Because I had the ear of someone who was willing to listen, we were able to recognise the signs early and make a plan," she said.

Whether you're working to break down silos between functions, encourage direct reports to speak up, or facilitate the free flow of ideas, here are some ways to avoid the dangers of yes people within your organisation:

Actively seek and reward feedback

Perhaps the best way to encourage your direct reports to give you feedback is to actively ask for it and receive it in a way that shows they can continue to be honest with you, Scott said.

"Convince your team you actually do want to hear what they really think," she said. "Show them that your requests for criticism are genuine and that you sincerely appreciate it when they say what they think."

Scott recommends leaders ask for criticism regularly and reward candour when received. It may take a while for direct reports to gather the courage necessary to give difficult feedback, which is why it's important to reward small wins along the way.

For example, Scott's request for feedback was consistently met with silence during team meetings, but eventually someone spoke up to complain about the tea in the office. In response, she thanked them publicly, wrote them a note by hand, and approved funds to get better tea for everyone in the office. Even relatively minor feedback like this can be used to show your entire team what happens when they speak up about workplace issues, she said.

Feedback can also be collected through company-wide surveys, which can be anonymous to eliminate any fear of retribution. The key to encouraging employees to speak up about issues in surveys is to take the feedback seriously and implement any common-sense requests immediately.

Kirsten Duke, CPA, CGMA, the CFO at DomainTools, based in Seattle in the US, said an organisation-wide survey helped company leadership recognise that employees were fearful of coming back to the office while COVID-19 continued to pose a risk and a vaccine was not available.

"We listened to this feedback and made the decision that employees would be able to continue to work remotely through the end of the year, at which time we would assess the situation for next steps," she said.

Get an outside perspective

Employees are sometimes afraid to confront their boss directly about an issue, but they might be more willing to express their concerns to a third party, Duke suggested.

Earlier this year, DomainTools conducted an organisational assessment, where they brought in an external consultant to ask each of their employees what was contributing to their doing their best work and what was getting in the way of their best work. The consultant then took those themes and reported back to the company leaders, who created task forces made up of employees to help determine how they could best address the identified issues as an organisation.

"Having the leaders determine how to best address these issues wouldn't work," Duke said. "These are themes that were brought up across the organisation, and the employees across the organisation are the ones that we need input from on how to best solve them."

Conduct skip-level meetings

If you're a manager of managers, and you're concerned that the people who work for your direct reports are having trouble voicing concerns, Scott recommends conducting skip-level meetings once a year to help overcome the challenge of hierarchy. During a skip-level meeting, you meet with the people who work for each of your direct reports to give them an opportunity to give feedback about their boss. The feedback is then compiled and shared collectively with the manager so they know what was said but not who said what. This ensures the team is comfortable criticising their boss without fear of retribution.

"Through this process we get to hear what concerns there are across the organisation," Scott said. "Feedback typically comes back loud and clear through these questions. We can take that feedback and listen to those voices to make changes for the better of the organisation."

This process not only helps uncover voices from all levels of an organisation, but it can also help make your direct reports better managers. During these meetings, you can collect candid feedback on a wide range of issues that can then be used to improve the organisation.

Experiment with role-playing

One way to encourage team members to consider a variety of perspectives and avoid settling on the ideas proposed by leaders is to experiment with role-playing, according to Michael Roberto, DBA, Trustee Professor of Management at Bryant University in Smithfield, Rhode Island, in the US, and author of Why Great Leaders Don't Take Yes for an Answer.

Roberto has done a number of decision-making case studies on businesses across industries and has witnessed a few highly effective role-playing experiments that encouraged team members to view issues from fresh perspectives.

When one company was trying to decide on a strategic alliance, for example, the CFO had the team role-play the competition, prompting them to consider what the reaction might be if they were to form each alliance and what consequences they might see down the road after doing so.

In another exercise, the CFO and other members of the finance team took on the perspectives of marketing, sales, and operations, while marketing, sales, and operations team members looked at issues from a finance perspective.

"It got this robust dialogue going, and it opened people's eyes," Roberto recalled. "Making people stand in each other's shoes turned out to be a great way of helping the team understand each other's perspectives."

Any exercise that encourages team members to consider new perspectives or propose additional options can arguably help reduce the likelihood of echo chambers and increase effective business partnering.

Get creative with meetings

Holding meetings outside the confines of a conference room can help eliminate oppressive formalities and encourage a free flow of communication. Martin is a big fan of walking meetings, and she has often had her teams walk together from the office to a nearby coffee shop as they discussed both personal and work-related topics.

"It was a little bit social, little bit catching up, but if there was anything that was on anybody's mind, it was a really good time to bring it up," she said. "The conversation was much more open and didn't feel like a conference-room meeting — it's about creating that environment where communication is flowing back and forth among everybody."

Take the stigma out of mistakes

Everyone makes mistakes, but when employees or leaders try to hide or minimise their blunders, it's impossible to address and learn from them in a timely manner.

"In construction there's a saying that we love good news, don't mind bad news, but hate surprises," Martin said. "Don't surprise me — 99.9% of the time it can be fixed a lot quicker if we just do it now."

In order to destigmatise mistakes and encourage everyone to speak up about issues, Scott sometimes plays a game she calls "Whoops-A-Daisy" with her team.

To play the game, leaders bring a stuffed daisy flower to their next team meeting and share a mistake they've made in the past week. Then she opens the floor to the entire team and lets them know that anyone who tells a story gets automatic forgiveness.

In Scott's version of the game, the person who tells the best story, as measured by the level of applause, wins "Whoops" for a week and $20. She explained that the $20 prize is primarily to give team members a reason to play along with her game. And the part where leaders share a mistake of their own is an essential component of the game because the team will feel much more willing to share their blunders once the leader has demonstrated vulnerability.

"Starting this process and getting people comfortable with sharing their mistakes is extremely valuable for creating a culture of feedback and learning," Scott said.

Step out of the room

It can sometimes make a huge difference when the leader steps out of the room and allows the rest of the team to talk amongst themselves, according to Roberto.

If your team seems to have hit a wall, he recommends summarising the issue, telling them you want some options and an evaluation, and then stepping out of the room for a bit.

"Once you're in the room, the whole dynamic changes," he explained. "Stepping out of the room sometimes can be a great way to give people a chance to get their thoughts in order."

Perfect your poker face

Team members are only going to freely express their opinions if they feel psychologically safe enough to do so, and a key part of achieving that psychological safety is reacting appropriately when people do come forward with a problem or say "no".

Roberto stressed that leaders should never tell their employees, "Don't come to me with problems, come to me with solutions."

"This is horrendous leadership because what you're basically telling people is hide the problem unless you have it all solved," he said. "That's terrible because you want people to tell you what's going on."

Instead, leaders must do their best to react calmly to bad news and work with their teams to develop collaborative solutions. When you react, consider not only your words, but also your tone and body language.

"Take a breath before you answer," Martin suggested. "And then find out why the mistake happened, because it could be that a company process is the problem; but either way, we definitely don't want people to try and hide issues."

Hannah Pitstick is a freelance writer based in the US. To comment on this article or to suggest an idea for another article, contact Drew Adamek, an FM magazine senior editor, at



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