Five steps team leaders should take to prepare for difficult conversations
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Five steps team leaders should take to prepare for difficult conversations

Few people enjoy giving negative feedback, and that is especially true when it is a manager reviewing the performance of a team member.

Those tough conversations are often part of the cultural fabric of big companies, where both physical and invisible walls separate people on different rungs of the hierarchy. But in early-stage startups, where founders work alongside and often socialize with engineers, product managers, and marketers, those conversations can be more challenging.

During a recent roundtable discussion in Tel Aviv sponsored by Samsung NEXT, a group of entrepreneurs identified assertiveness as one of the traits managers and team leaders at early-stage startups need to develop in order to handle tough conversations with employees.

As part of its mission to be a value-add investor, Samsung NEXT Tel Aviv invited team leaders and managers from five of its portfolio companies to workshops on team management.

The leaders learned about and collaborated with one another on developing a managerial approach, team building, developing management assertiveness, and creating engagement through positive psychology.

The challenge of open conversations
In their 2009 New York Times bestseller Start-up Nation, Dan Senor and Saul Singer argue that mandatory military service is one of the keys to Israeli’s success in nurturing high-tech companies.

The authors note that elite military intelligence units serve as the breeding ground for startup founders. These units employ a relatively flat organizational structure where performance matters more than rank and commanders sit side-by-side with subordinates – and graduates import this structure into their startups.

The typical Israeli early-stage startup is housed in an open space of 20 to 80 people where managers and employees work side-by-side, according to Yael Ran, Samsung NEXT’s head of HR in Israel. This flat, informal working environment can be more conducive to getting things done but may not always lead to candid discussions between managers and employees, she says.

“When you work in an open space, you have a good idea of what your manager is doing, what your co-workers are doing,” she says. “It’s an amicable, friendly work environment. Some of the leaders are managing people they served with in the military and have brought with them to their company. It all sounds really fun, but we think it creates a challenge for the managers in some cases.”

The main problem for managers is in finding ways to have authentic conversations with team members, Ran says. “You hire these highly sought-after talents who join your startup in a highly competitive environment,” she says. “Usually, they join you because the technology is cutting edge or they get to build something from scratch. But sometimes the work isn’t as sexy. The system might be failing, they might have to stay longer hours doing mundane tasks, doing dirty work.”

In Samsung NEXT’s leadership course, managers learned the five steps to having frank discussions with employees.

1. Emphasize the importance of the discussion

Don’t surprise an employee in the hallway, don’t delay, and don’t belittle them. Schedule a formal meeting in a closed room to emphasize the conversation’s importance. Most crucially, keep everything in proportion.

“This isn’t a pre-termination hearing,” Ran says. “This is to improve the work going forward. You need to think about the day after this conversation. Tomorrow you’ll need to sit in the same room as this person. The way you convey your message must allow you to keep working together.”

2. Prepare talking points

Give very specific feedback, focusing on what the task was and why it wasn’t done properly. The feedback must be detailed, authentic, and delivered in a manner that encourages the employee to improve the next time.

“Introduce the topic at the beginning,” says Ran. “Don’t freestyle. If you know this is going to be tough for you, then prepare.”

3. Share motivation and context

Explain why it was important to depart from the daily routine and allocate time to a one-on-one conversation. Emphasize the importance of this task and the employee’s role in getting the task completed.

During the course, Ran and her group role-played a scenario where a manager felt guilty about having to ask an employee to work over the weekend. “The manager has to explain the purpose of the task, why there are no alternatives, and why this employee is the one who needs to do it,” she says.

4. Suggest a solution

Tell the employee what you would have done differently in this scenario. By suggesting an alternative way to handle the problem, you get an opportunity to show the employee the standard expected of them.

“It’s tough for managers,” says Ran. “You don’t want to micro-manage. You’re engaging high-performing individuals, but in some cases, you do need to manage. And managing is also about indicating what the standard is.”

5. Be empathetic

Before closing, express confidence in the employee’s ability to complete the task. Speak clearly and don’t sugarcoat your comments.

“You’re empowering the person,” says Ran. “You trust that they can do it. You’re not reprimanding them. At the end of the day, you’re a manager, and that’s what the manager does.”

Assertive managers are confident but not arrogant
An informal work environment is ideal for getting things done but it can occasionally cause managers to forget their role, says Ran. And managers must recognize that managing is a part of their job description, even if it doesn’t always come naturally.

“A lot of managers feel guilty about conveying tough messages or holding other people accountable. If you convey yourself as authentic, confident, but you’re not arrogant–that’s the mindset the manager should possess,” says Ran.

When planning a tough conversation with an employee, preparation is key. Having prepared talking points — constructive feedback for the employee, an outline of the problem, proposed solutions, and some kind words to use at the end — ensures the conversation stays on point and increases the odds that the employee cooperates.


To learn more about ecosystem knowledge-sharing events and how to work with Samsung NEXT in Israel, visit our Tel Aviv page. To stay up-to-date on activities globally, please sign up for our weekly newsletter.

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