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Learn how middle and senior managers can build trust with staff by using a popular and effective executive tool — the skip level meeting 🤝


Employees consistently rate ‘trust’ as one of the most important attributes for a senior manager. Unfortunately, over 30% of employees say that trust in their senior managers is weak, and 45% of employees say that a lack of trust in leadership is the biggest issue impacting their work performance.

That data comes from Claire McCartney’s report ‘Employee Outlook: Trust in Leaders’. In her report, Claire comments that “There seems to be a real lack of awareness amongst senior managers, who rate the trust levels much stronger than more junior employees. It seems they either have a tendency to view things through rose-tinted glasses, or are out of touch with how employees nearer the coalface are feeling. If senior leaders are in denial or burying their heads in the sand, there is a danger that a ‘them and us’ mentality will emerge and change will be very difficult to achieve.”

When employees don’t trust their leaders, they feel unsafe. They’ll avoid risks, waste time on self-preservation, and they’ll probably leave as soon as they can find a new job. On the other hand, when employees trust their leadership, they feel supported. Well-supported employees take good risks, share bold new ideas and make their leaders aware of problems. As a result, senior leaders with strong connections to the front-lines can identify and resolve problems quicker, develop products that serve clients better, and retain their staff more effectively.

It’s clearly in a senior managers best interest to build trust with the front-line staff — but how? This article will help middle and senior managers build trust with front-line staff through a popular and effective executive tool, the ‘skip level meeting’.


What is a Skip-Level Meeting?

The skip-level meeting is a conversation between a middle or senior manager and the employees who are supervised by their direct reports. For example, a General Manager of a retail store manages 5 department supervisors. In a skip level meeting, the General Manager will meet with the employees who report to her department supervisors, thereby ‘skipping a level’.

The purpose of these conversations is to connect the organizational decision-makers with the front-line workers. These conversations are an opportunity to build trust, get to know their team members and to gain valuable real-time insights from the front-lines.

Senior leaders can choose to discuss the goals and development needs of those employees, ask specific questions or simply listen to the ideas and concerns they have. I suggest offering discussion topic prompts in advance, but allowing the employee the freedom to discuss whatever they feel is important.

Who Should You Schedule Skip-Level Meetings With?

Employees should be focused on understanding the job and building confidence through the first six months of their role. Therefore, I recommend scheduling skip-level meetings exclusively with employees who have been in their positions for more than 6 months.

Scheduling the first few skip-level meetings with your most amicable and enthusiastic employees; this will help you get comfortable and build confidence in facilitating these conversations. Once you’ve gotten comfortable, schedule some meeting with folks who you are less comfortable with, or who are known to have ‘bigger personalities’.

It will likely be unfeasible to meet with all employees two levels down from you, so be comfortable purposefully selecting specific employees. Be brave and select a range of employees with different views and temperaments, not just those who perform well or who you are comfortable with.

When Should You Have Skip-Level Meetings?

You might implement skip-level conversations as an informal or ongoing practice. Alternately, you may choose to have them within a window of time as part of a strategic planning cycle.

I suggest choosing a month in which you would schedule all of your skip-level meetings. This will be easier on you and your direct reports in terms of planning and logistics. I also suggest you host your skip-level meetings in a month or two preceding your annual or bi-annual performance reviews. Performance reviews typically include a goal-setting component, and the questions you ask and the wisdom you share might inspire them to aim higher or be open to new possibilities.

A pre-existing sense of familiarity will help you to get more honesty and openness from the employees. Therefore, you should host these conversations after you’ve created some form of regular contact or visibility with the employees. Well ahead of time (2+ months), make a daily habit of walking around amongst the staff, striking casual conversations, making some jokes and being approachable.

How Do You Organize a Skip-Level Meeting?

This exercise will make people feel vulnerable, so you need to communicate very effectively with both the manager of the team and the employees throughout the process. What you don’t want to do is surprise anyone — after all, the whole purpose of these is to enhance communication and build trust!

Start by meeting with your direct-reports to make them aware of your intentions. Tell them why you are hosting these conversations, what you intend to discuss and what you will do with the information you get. Depending on your familiarity with their teams, you may even want to ask whom they suggest you meet with first.

After you’ve met with your direct-reports, offer advance notice to the employees with whom you’ll be meeting. Share the logistical information (I recommend scheduling an hour in a private area), any discussion prompts, and be very clear about the goals of the meeting. You want to be as friendly and encouraging as possible — for most employees, an invitation to meet with their boss’s boss is a scary thing.

Ahead of the meeting, ensure that you fully understand the employee’s role, what their accountabilities are and how they contribute to the business objectives.

What Should You Discuss at the Skip-Level Meeting?

Each employee is different, so you’ll want to consider their specific circumstances when choosing discussion topics. Considerations could be their current role, their history with the organization and the stage of their career.

Regardless of their circumstances, you’ll want to invite employees to share what they are passionate about and ask open-ended questions about their strengths, career aspirations, previous work experience, and areas where they would like to develop. You’ll also want to ask what leadership could do that would help them achieve their goals.

Ideally, you’ll have some wisdom to share as well. Therefore, it’s a good idea to invite the employees to take notes (though don’t insist — this isn’t a performance management meeting!).

General Questions:

  • “What are you passionate about in your current job?”
  • “What works well in your department?” (eg processes, policies, incentives, etc)
  • “What needs improvement and/or what obstacles are preventing you from being successful?”
  • “What is one thing the business should start doing to be more successful?”
  • “What is one thing the business should stop doing to be more successful?”
  • “What supports or opportunities in the workplace would you to achieve your career goals?”

Also, here are some questions that are catered to the individual’s disposition in their role:

New to the Organization

  • “What difference do you want to make?”
  • “What opportunities do you see for yourself?”
  • “How do you want to grow and develop?”

Mid-Career

  • “Where do you see yourself in x years?
  • “How would you define “success” for your career?
  • “What impact do you want to have in your work?
  • “What kind of leadership style challenges you to be your best?
  • “In what areas do you want to grow?
  • “What types of work do you want to do more of?
  • “What one thing could I do to better support your career development?
  • “What will keep you engaged?”
  • “What inspires you to do your best?”

Close to Retirement

  • “What do you want to be your greatest contribution?”
  • “What will others say has been your greatest contribution?”
  • “How do you want to contribute in your final months/years?”
  • “What knowledge and skills do you have that could be useful to others? How can you pass them on?”

How Should You Follow-Up?

Since this meeting is about building trust and fruitful connections between front-line staff and senior management, you must show appreciation for the employees’ time and keep them informed about what is being done with the information that they’ve given you. Elsewise, you risk giving the impression that you just used them for intel, and don’t actually care to support them. This can put you in a worse position than you were before you started.

I recommend that you send a follow-up email to the employee shortly after the meeting the thank them for their time, offer your appreciation, and let them know what the next steps are. You don’t need to be very detailed, and certainly, don’t make any commitments that you aren’t sure you can keep. Something like this would suffice:

“Hi (employee name). It was a pleasure speaking with you today. I want to sincerely thank you for the time and honesty you shared with me. Your thoughts and perspectives are very valuable, and they’ll help me and the rest of the leadership team to make more informed decisions around the policy and practices of our workplace. I look forward to chatting again in the near future.”

After you’ve hosted your skip-level meetings (ideally you will have done 5 or more), compile your data and organize it into any themes that emerged. Conduct analysis and draw initial conclusions from the data, and consider what people or process issues you can and should improve.

Once you’ve completed your analysis, share your data and findings with your leadership team for discussion (keep specific employees confidential though). Allow your leadership team to interpret and analyze the findings themselves, ask questions and discuss the opportunities and next steps you can take together.

Objectivity is the key to creating the results you’re after, so be aware of your own biases and blinds-pots and be humble — this will help you be as objective as possible with your analysis.

If specific actions come out of your findings, be sure to get back to the employees personally to let them know. This helps solidify the relationship and trust you’ve built with one another, it gives credibility to the concept, intent and potential outcomes of the skip-level meetings.


Final Thoughts

This article has offered a good starting point to the trust-building process between senior leaders and front-line staff.

However, whether the exercise is a success or not depends on whether the individual conducting the meetings has taken steps to create a comfortable environment, is ready to listen attentively, and willing to be told that they are wrong about many things.

Conducting the meetings is not a success unto itself. It will open up vulnerabilities across the organization that had previously been covered up. The leader will need to be willing to check in with the employees from time to time, let them know the impacts of their input, and take action where it’s due. If the leader is not willing to do this, it might be better not to have the meeting in the first place — status quo would be better than encouraging your staff, only to let them fall further into mistrust than they were in the first place.

However, if you are willing to conduct these meeting in good faith, stay connected with your staff, and take action to improve your organization, then these meetings will give you a tremendous competitive advantage immediately and into the future.

Thanks for reading!



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