Great One-On-One Meetings

Izzie Egan

…Or How to Get the Straight Goods on What’s Happening

Some managers think of one-on-one meetings as those awkward things that HR forces on them as part of “performance management”.  Another way to think of them, however, are as part of the overall communication strategy for the company and a way to get to know your team members personally, as well as allowing them to know you and how you tick.  A company can have standups, townhalls, team meetings, email and instant messaging tools, all of which are good for top down or formal communication, but nothing replaces actually getting to know who you are working with and how they think.  One-on-one meetings, provide a different, more personal and private way for information and ideas to flow UP the organization (note we say flow up, not down). Regular one-on-one’s are also a key component of a successful coaching relationship with employees and should form part of any performance process.



We often hear from both employees and their managers that one-on-one’s are a waste of time and ineffective. On the other hand, we also hear from people who want to know more about how to run effective one-on-one’s.  Maybe both groups are talking about two sides of the same coin and it’s a skills gap, rather than a problem with the process.  After all, who wakes up knowing how to be a great coach, or has had the chance in their working life to be mentored by one?  If as a leader you are interested in hearing what’s going on at all levels in the company, one-on-ones may be a great way to get the inside scoop from the people who are really in the know – the employees.

If you’ve been the victim of a poorly designed one-on-one meeting you will know how painful they are. The key to a good one-on-one is the understanding that it is the employee’s meeting rather than the leader’s. This is the free-form meeting for all the pressing issues, brilliant ideas and chronic frustrations that have no other venue.

Source: Gratisography
Source: Gratisography

How often is often enough?  We recommend one-on-one meetings be scheduled every two weeks with each team member.  It’s a big time commitment, but it will pay big dividends.  The meetings should be set in advance – get them in both your calendars and commit to honouring the time, no matter what, because “urgent” never goes away. If you travel, have remote workers or flex time, you can use tools like Hangouts or Skype. If you work together, change location, go for a walk or get outside.

We like to have an agenda (‘Structured Time’ sounds so corporate, but it really helps,) it keeps the purpose and conversation clear.  Having said that, the employee should set the agenda (not vice-versa) and in a perfect world, send it to you in advance so you know what they want to chat about and be able to provide them with useful and thoughtful answers.  This makes it clear that it is their meeting. A solid guideline is during the meeting the leader should do 10% of the talking and 90% of the listening.(We call this ‘holding space’ for everyone to have a voice. (Note that this is the opposite of most one-on-one’s.)

Managers who want to hear the straight goods from their team first have to build solid relationships based in trust and create a safe environment for open feedforward. If you have never had any training or coaching on giving and receiving feedback/feedforward, investing in improving those crucial skills is as important as investing in better web analytics.


And until those high trust relationships have a chance to develop, leaders may have to dig to draw out the key issues. The more introverted the employee, the more important this becomes. If you manage a technical team, drawing out issues will be a key skill to master.

In case you thought this didn’t apply to the top dogs, let me emphasize that it’s critically important for founders and senior leaders to schedule regular check-ins with their  team members.  If you want the information to flow all the way up, the top has to be listening. Bottom line, If you are “managing” anyone, you should be having regular coaching conversations with them.

But who do founders and CEO’s talk to?  Look for a trusted advisor, a mentor or a member of your Board that you can pressure test your ideas with and who you trust enough to receive honest feedback/feedforward and insights from.  Another resource could be a professional business coach, an investment well worth considering and one both BLANKSLATE cofounders believe in.

So all that advice is GREAT, but how do you do it?  Here are some questions that are great for drawing out all those emergent ideas and concerns:

  • Are you happy working here?
  • If we could improve in any way, how would we do it?
  • What’s the number 1 problem with our company? Why?
  • What’s frustrating about working here? What sucks and how would you change it?
  • Who is really kicking ass in the company? Who do you admire?
  • If you were me, what changes would you make? What can I do differently or improve?
  • What don’t you like about our product/service?
  • What’s the biggest opportunity that we’re missing out on?
  • What are we not doing that we should be doing?
  • What do we need to stop doing?
  • What could I do differently to support you/what do you need to achieve your goals?
  • What are you working towards personally?
  • Do you have the resourced you need?

Of course you are also going to check in on how your team is going against their Objectives and Key Results, as well as their personal goals.

Some questions can help guide the conversation are:

  • Tell me about your week – what has it been like for you? What’s going on in your life?
  • Tell me about what you’ve been working on
  • Where do you think I can be most helpful?
  • Are you on track to meet the deadline?
  • What areas are ahead of schedule?
  • What questions do you have about this area of responsibility or project? Do you know how you are making an impact for the company/project/team?
  • How are you going to approach this?
  • What didn’t go as you had hoped? Why?
  • What can you/we do differently next time?

Like any well managed meeting, a one-on-one should end with both employee and manager confirming any agreements they have made and what next steps are required by either of them.  And the old maxim of “if it’s not written down, it didn’t happen” could not be more true.  There are a lot of great tools and resources out there to help companies manage the one-on-one process.  HRIS systems like BambooHR have built-in performance management tools.   7Geese is designed specifically around continuous feedback and coaching and Impraise has a mission to let employees drive performance management and coaching.  Or there are project management tools likeAsana and Trello that you can use to follow up with to do’s and actions needed to be done. Share the task, get everyone committed to the timeline and talk about it!

In the end, what’s most important is that people talk. Companies like lululemon use terms like “get into relationship” when talking about building manager and team member rapport. It’s great advice, but it can be overwhelming for new managers. Our advice – start listening. Ask good questions and care about the answers. If everyone does this, and everyone is responsible for their part of the relationship, the best ideas, the biggest problems and the most intense employee issues make their way to the people that can deal with them and one-on-one’s are a time-tested way to do that.

Some books to read that are great for building managerial skills and understanding culture:

  • “Leadership and the 1 Minute Manager” – Ken Blanchard
  • “Delivering Happiness – A Path to Profits, Passion and Purpose” – Tony Hsieh