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Virtual leadership coaching: How to assess and coach for success


With the widespread prevalence and acceptance of remote work, senior managers are confronting a fresh challenge with frontline managers: How to tackle virtual leadership coaching?

For instance, you may be wondering:

  • How can I help managers improve their performance and skills, and ultimately lead their teams better, in this not-so-temporary situation?
  • If I’m not physically in the office with my managers, how do I even discover problem areas to start with?

With the distance between colleagues and the inability to witness firsthand how a manager performs all day, senior managers have the difficult task of trying to ascertain:

It’s the same situation that these frontline managers face with their employees.

After all, individuals have responded differently to remote work. Some are thriving, enthusiastic about the lack of commute, newfound flexibility and increased work-life balance. Others feel off kilter, struggling with the solitude and feelings of disconnectedness from their teams, in need of more structure and unable to separate work from their personal life.

Managers are no different.

How virtual leadership coaching can challenge and benefit managers

Certainly, virtual workplaces have changed how frontline managers interact with and oversee their teams. Some managers may be comfortable leading others in a traditional office environment, but other managers aren’t sure how to lead in a virtual workplace and feel lost.

Frontline managers have commonly reported that they struggle with:

  • Reading their employees and picking up on their subtle cues over videoconferences, phone calls and email
  • Not being able to walk around the office and check on direct reports in person
  • Trusting employees, given their inability to verify whether, or for how long, an employee is actually working
  • Not being able to exert more control over when tasks or projects get done
  • Needing to schedule formal meetings with direct reports more often versus engaging in spontaneous, casual conversations
  • Shifting their focus away from hours worked toward productivity

Clearly, for managers who are more controlling and task-focused by nature – also known as micromanagers – the transition to remote work has been more stressful.

But these challenges aren’t all negative – in many cases, they’ve prompted managers to identify their shortcomings and improve their performance.

From these challenges, it’s clear which critical skills frontline managers need to be successful in virtual workplaces:

  • Active listening skills, and the ability to infer what’s being said “between the lines”
  • Emotional intelligence (EQ)
  • Empathy (gaining the perspective of employees as “people first and employees second” and being flexible about enabling employees to balance work with personal and family obligations)
  • Servant leadership
  • Ability to get everyone on their team to participate in and contribute to virtual meetings, on camera
  • Acceptance of less control
  • Ability to bring a sense of continuity and a mindset of resiliency to their teams, especially during periods marked by turbulence and uncertainty

5 ways to assess frontline managers’ performance

So, how can you determine how a manager is performing from a distance?

1. Have an open-door policy

If implemented well, an open-door policy can be a great way to find out what employees think of their manager’s performance or to uncover any potential issues, on an ongoing basis.

An open-door policy is when companies encourage employees to go to their managers with any questions, concerns or discussion of specific issues. Employees can either go to their direct manager or, if they don’t feel comfortable doing that, to the next level of management (their manager’s manager).

In a traditional office environment, the policy essentially says, “My office door is open. Talk to me (or call or email me) anytime.” As an alternative, some companies have a box in which employees can submit anonymous notes.

Of course, in virtual workplaces, employees need to set up a video meeting or phone call, or send an email.

Generally speaking, most companies will say they have an open-door policy. However, how comfortable your employees feel in taking advantage of this policy has much to do with your workplace culture. It takes a lot of trust for employees to leverage this option.

Employees need to know who they can contact up their direct chain of command and, especially in virtual workplaces, how to reach these senior leaders. Employees need assurance that their feedback is encouraged and valued.

2. Conduct employee or team surveys

Surveys are another great feedback mechanism that you can implement on a regular basis.

Issue surveys to your employees, either to individuals or to entire teams. Survey questions can be customized according to the manager and can be completed electronically and anonymously.

The downside is that you run the risk of high numbers of employees not participating because they don’t trust the survey’s confidentiality. This is especially true at smaller companies.

3. Perform a 360-degree assessment

In a 360-degree employee review, you identify different, important relationships for each manager at various organizational levels, both within or outside the company – such as a subordinate, peer, superior and a third party (ex., vendor). Then you send these individuals a manager evaluation. This enables you to get a comprehensive and likely more objective view of a manager’s performance. This option can be more costly and time consuming.

4. Hold periodic skip-level meetings

A skip-level meeting is when employees bypass a rung on the organizational ladder and, instead of meeting with their own manager, meet with their manager’s manager.

This type of meeting offers key benefits for senior managers:

  • Allows them to learn from employees firsthand about any important topics or issues of concern
  • Gives them an opportunity to build relationships with lower-level employees, which is critical for employees’ career progression and succession planning
  • Helps them to obtain the perspective of frontline managers, as well as capture a different view of the direct manager

5. Enlist a customized management assessment

Administered by performance specialists, customized assessments involve interviewing managers, evaluating their mastery of specific skills and compiling data to calculate a score. It can be a time-consuming and costly process, but is effective in determining a manager’s skill level, performance strengths and weaknesses, and whether they meet organizational standards.

How to help managers improve

Once you’ve identified issues or opportunities for improvement, how do you proceed?

1. Define clear expectations

Be specific about which skills require improvement, and why.

Explain what improvement looks like, and what constitutes successfully meeting this goal.

Lay out a plan for how the manager will achieve the improvement.

2. Provide an appropriate timeline for them to make changes

Be realistic. You’re trying to develop a person, so you need to give them ample time to modify behaviors. This usually doesn’t happen quickly (e.g., within a month) – especially in a virtual workplace.

3. Offer necessary resources

Coaching is a skill. If you’re not able to coach a manager, find a qualified professional who can or a resource that can assist.

Perhaps a manager may benefit from a mentorship with a more senior manager.

Or, perhaps they need leadership coaching and training. There are all types of virtual leadership training programs or courses to which companies can subscribe.

A few points to keep in mind:

  • Not everyone responds effectively to virtual training – they can become easily distracted. Managers who enroll in virtual courses must be independent, self-directed learners to be successful.
  • Avoid general leadership training, which is often too broad in scope to be useful. If you know a manager’s weak spots, find training courses that address those specific skills. Shorter, more focused bursts of education tend to be more effective anyway.
  • Live, instructor-led virtual training courses tend to be more effective than pre-recorded training.
  • Accountability is essential – and it’s often an issue with virtual training. You want to ensure that your managers acquire the knowledge and skills they set out to obtain, and that they got some meaningful information out of the course. So, hold people accountable for what they learned. Ask them to teach you about the topic.

Some professional employer organizations (PEOs) offer specialized leadership coaching.

Instill a culture of continuous learning in your workplace in which managers make it a regular practice to develop certain skills on their own initiative before problems arise. This activity could be as simple as reading a book on a specific leadership skill.

If a manager asks you for more support, be available to:

  • Answer questions
  • Provide additional resources
  • Offer feedback
  • Redirect their efforts if they’re going astray

4. Incorporate coaching into performance evaluations

Rolling coaching conversations into performance evaluations is a powerful motivator for managers. Why? Because meeting performance objectives and other goals are tied to bonuses, salary increases and promotions. When a financial benefit exists, managers can be enticed into accepting coaching and modifying their behaviors more quickly.

3 ways to keep managers engaged

When a manager is facing challenges with leading in a virtual workplace and knows they have skills to improve upon, how do you motivate them, boost their confidence and maintain their connection with your company?

1. Tell them to lighten up

This is one of the most important messages that frontline managers need to hear.

Tell them:

  • Everyone’s different and has handled the stress of working remotely differently. That’s OK.
    • Nobody’s perfect.
    • Be yourself with your direct reports. Remember that you’re a person, too. Vulnerability builds trust and can bond you with direct reports, which help to build better relationships.

2. Communicate – and check in on a one-on-one basis

Senior leaders should model good communication. Upper management should communicate regularly with frontline managers to ensure they have everything they need. This also provides an opportunity for leaders to discover (and perhaps sidestep) potential problems.

Check-ins should happen at least once per week, optimally. In fact, the frequency of meetings between senior and frontline managers may need to be higher than that of meetings between frontline managers and their direct reports.

3. Hold regular strategy meetings for all leaders

In addition to frequent check-ins between senior managers and frontline managers, the entire management team should meet as a group at least once per month to share ideas and discuss organizational plans. This can help to remind managers of their role within a company and how they contribute to reaching goals, which can increase engagement.

Summing it all up

As it is with all other employees, virtual leadership coaching can be a challenge, given the physical distance and reduced oversight between senior managers and frontline managers.

Virtual work has complicated the role of frontline managers and has created many challenges – but it has also revealed which skills are critical to have for successful remote management, along with opportunities for improvement.

  • To find out how your managers are struggling and how employees may be impacted, leverage your company’s open-door policy, employee or team surveys and skip-level meetings. Or, depending on timeline and budget, consider more extensive manager evaluations.
  • When coaching managers, be clear about your expectations, allow enough time for behavior modification, provide necessary resources and consider incorporating accomplishment of certain goals into performance evaluations – and tying these goals to financial incentives.
  • Lastly, to keep managers engaged and confident, communicate with them often and schedule regular check-in meetings. Let them know that it’s OK for them to show vulnerability with their direct reports.

To learn more about developing your organization’s managers, download our free magazine: The Insperity guide to leadership and management.