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5 Best Practices For Strengthening Your 1-On-1s

In the age of remote work, individual conversations with your direct reports have never been more important. Here's how to make them work for you.

A good bit of data and many years of observation suggest that CEO one-on-one discussions with direct reports can have a surprisingly large impact on a leadership team’s performance. In their Project Oxygen study Google found that higher-scoring managers were more likely than lower-scoring managers to have frequent one-on-one meetings with their direct reports. According to Gallup’s State of the American Manager report, employees (yes, even executives) who have regular meetings with their supervisors are three times more likely to feel engaged and thrive at work.

This all makes a lot of sense when we step back and reflect on the foundational elements of building any relationship. Relationships are built on trust and trust requires time, give and take, and vulnerability. And just like with any good habit – think exercise and dieting – getting our desired results requires practice and repetition. Executive relationships are no different and one-on-one discussions can be a very useful tool for accelerating and helping them thrive.

This is especially true in today’s environment where many are working remotely and the stress of personal life and running a business is heightened. Much has been written recently about the transactional nature of our daily work life that includes a preponderance of video and conference calls. One-on-one discussions have perhaps never been more important for ensuring that leaders move beyond running the day-to-day and engage with greater foresight and developmental thinking.

Unfortunately, we often hear CEOs and their direct reports refer to one-on-one discussions as ineffective or just a waste of time. Below are some direct quotes that reflect sentiments of some leaders…

“We start with good intentions but inevitably we default to putting out the latest fire or resolving a specific tactical issue.”

“He (CEO) tends to dominate the discussion with complaints which might be related to what’s most important to me but often are not.”

“My direct reports rarely come prepared with substantive discussion points and I have to carry the meeting.”

“I leave these discussions with little to no sense about how I am doing and what I could be doing to get better.”

“I feel like she (CEO) is doing these one-on-one’s because HR told her to as she is often not very engaged or attentive.”

If deployed thoughtfully, one-on-one’s can be a very powerful tool in a CEO’s arsenal; they can help solidify or course correct strategic direction, help executives become better teammates and leaders, and serve as early warning for a host of potential challenges and obstacles. Elizabeth Grace Sunders, author of How to Invest Your Time Like Money suggests that “one-on-ones are one of the most important productivity tools you have as a leader. They are where you can ask strategic questions such as, are we focused on the right things? And from a rapport point of view, they are how you show direct reports that you value them and care about them.”

“One-on-ones are where you can ask strategic questions such as, are we focused on the right things? And from a rapport point of view, they show direct reports that you value and care about them.”

Our experience suggests that the most effective one-on-one discussions should focus on three areas. First, they should help clarify expectations from the perspective of the CEO (‘how can I help you meet these expectations’) and the direct report (‘what can I be doing better/different to meet your expectations’). Next, time should be devoted to addressing the most important business priorities (‘I am struggling with how to resolve this issue and could use some advice’) and developmental priorities (‘I see progress but here are a few observations that I think could help accelerate progress’). Finally, effective one-on-ones should give direct reports as sense of support and care for them as employees and people (‘I know you have small children and that your husband is also working from home; how is that going and what can we do to help you’).

In addition to ensuring that your direct reports understand the purpose of your one-on-one discussions as described above, below are five best practices for ensuring they are as productive as possible.

1. Don’t wing it! – commit to a specific cadence (e.g., monthly for one hour), use a standing agenda (priorities, development, feedback, personal support), and come prepared and hold your direct reports accountable for being prepared.

2. Don’t put it all on your direct reports – come prepared to provide specific constructive input on priorities and development challenges; and don’t forget to check on their personal well-being.

3. Focus on what’s most important – this is not the time to review a laundry list of tasks; one-on-ones should focus on helping direct reports address important priorities including personal ones.

4. Be attentive – devote your full attention to mostly listening; avoid distractions such as looking at your cell phone or computer.

5. Don’t substitute – just because you spend time with your direct reports on day-to-day issues doesn’t mean you can forgo one-on-ones; as described above they have a unique and focused purpose and deserve appropriate attention.

One-on-ones are an important strategic tool for CEOs. Time invested in doing them well pay off not only with each individual, but with how your leadership team operates collectively.


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