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Luke O'Connor on... Sales pipeline & performance

  • Apr 4, 2024
  • 4 minutes

Luke O’Connor is the Senior Sales Manager at Cision, a global tech provider for PR, marketing and comms. With years of experience leading sales teams, his approach to coaching and developing his reps encourages autonomy and accountability, making for stronger and healthier sales pipelines.

Here, he speaks with Shelley Lavery, Jiminny’s CRO, about pipeline management, rep performance and sales leadership. 


What springs to mind when you think about pipeline management? 

I think for me it's around freshness, activity and understanding the ideal customer profile. So it's really looking into the pipeline and understanding how fresh is that pipeline, using tools that understand how long reps have opportunities open when they’re successful.

And then looking at that and being really strict with opportunities that are in pipe longer than that.

Asking - why is it there? Are we just holding on just to make it look good? Or are we working these opportunities effectively? 

A new sales team vs an experienced sales team

[A new sales team] a lot more diligent, they understand it’s a fresh start, the slate is clean so they can start building and being a lot more strategic.

I think sometimes when you've been there a while and you've got a huge pipeline you can get lost. 

A shift happened last year when it became difficult. People realized that if you've got a huge pipeline, you can't see clearly so they had to take that emotional choice to start pulling that down. One of my most senior salespeople has done that effectively now. They've got a real clean pipeline - it’s smaller but actually become a lot more effective.

I think pipeline management has changed in that way. Yes you can have a state that goes across the whole team, saying ‘we want to see three or four x your target’ but you've got to look at it from an individual perspective as well. You might have some individuals where if they are doing five or six x of target, they’re drowning in their own pipeline. Or you might have some people that do just two x and that’s their sweet spot. 

So for me, what’s been a real change is understanding the individual’s targets and what works for them. So when we’re coaching, we can find out their sweet spot and make sure they’re reaching that as a minimum.

It also becomes a way to start managing performance. And a good indicator so you can start to see before things do slip. For example, this person is building a huge pipeline and they won't be able to manage that effectively.  

How do you communicate the idea that there is a cost in holding on to a lead as much as there is to closing it?

It’s experience, I’ve been that person holding on for way too long because you get emotional about it. But being open as a manager, showing that you’ve never been perfect and that you have those stories helps them see things from a place they understand. 

What does a good pipeline review look like?

It’s a whiteboard session, to really understand what they’re working and comparing that to what the overall pipeline looks like. Asking the difficult question of ‘why is that there, if it's been over X days?’ etc. 

There are going to be unique stories. But as a manager, you have to ask those difficult questions so you know you’re comfortable with what’s in the pipeline. 

How involved do you get in ‘the sale’?

I like to make a call now and again! If you’re talking to your team about it and they see you do it, at least they can think ‘he’s given it a go’. And it's good to understand what’s happening, be part of the processes.

One of the mistakes I made at the start of management though was getting too involved in a salesperson’s deal. Because they then become reliant on that support. So you need to take a step back and know when to be involved and when not to be involved. People learn a lot from their own mistakes. So if you never let them make the mistakes, they’ll never learn from it. 

Knowing when to step in and when to step back is a gut feeling, it’s listening to the calls and finding a good time to give feedback. Not necessarily ‘getting involved’, but giving feedback, saying ‘let’s look at this together’ and challenge them. 

There’s many individuals where I know we have that healthy relationship - we may disagree at the start but it’s important for me not to dictate what happens. We need to get to an end point where we both think ‘that’s a good approach’. Generally, it’s 50/50, it’s taken both ideas to find a solution and they feel completely comfortable to move forward with it. 

I always think if you tell someone what they need to do, when they do it they won't be 100% because they don’t fully understand why they’re doing it. 

That’s something I worked on with Jiminy and the biggest thing I learned was the difference between feedback and coaching and having a set time for coaching, it’s important. 

Why do you think coaching is so sporadic in so many businesses?

I’m guilty of that - sometimes a week goes by where they’ve got something or I’ve got something or there’s an important deal. And it slips. But that’s where you’ve got to bring it back around and make sure it happens. 

Out Jiminny CSM, Giuliana, asked me ‘do you listen to a coaching call before the session?’, whereas I’d always listen at the time. But that made me think so we’ve changed it now where people listen beforehand and really listen, that makes them more open to coaching and to self-coaching too.

What qualities do you think make a great sales leader and coach?

Listening to others and being prepared to change your own ideas is the most important thing. You could be talking to someone and they could come up with a great idea, so you don't want to think ‘well I can’t take that because I’m the manager’. If your team come up with an idea, let them lead a session, give them the power to do that. 

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