Introduction
As a first-time Sales Manager you’re gonna have your hands full! Scaling the team, motivating them, getting visibility into what’s working and what isn’t, enforcing a culture of accountability AND getting sucked into tons of cross-functional meetings in the meantime?
It’s a 65 hour per week job! Crazy - but also rewarding if you do it right. I tried a ton of things on the fly but one of the small things that made a big impact was Monday morning kickoffs.
When I was promoted to Management we were scaling both the teams and processes. Building out new processes is challenging enough, but needing feedback from new reps who don’t know what good should look like yet?
At times it took 4 weeks before I found out part of the process was broken and that played a role in KPIs being down. (Ouch!)
Also sadly not everyone was applying feedback or putting in the work necessary to hit targets. I needed a way to create visibility and nurture accountability within the team. Monday kickoffs helped just enough. In this post we’ll cover how to structure these meetings and how long should they be, what format to use so it scales, and what I’d do differently now after having talked to other sales leaders these past months.
How to structure weekly meetings
Let’s look at the structure and duration.
Firstly I had to consider that not many people love Mondays, and sales reps especially dislike meetings that take time away from selling. I know because I’m one of them.
Secondly I needed a way to create a culture of accountability and drive urgency and focus so we act on what needs to get done without getting sidetracked.
With that my main goal was to keep these meeting short and sweet while also making it valuable by enabling the team to sell better by attending.
By the end of the meeting I wanted the team to have visibility into what needs to get done while feeling empowered and motivated to get going.
The meeting had 5 parts:
Status update
First up we had a status update on where we stand on attainment versus target, what movement we had in pipeline in the past week, and had a look at the outbound leaderboard so top performers got recognition and lower performers had nowhere to hide. Does this mean we shamed low performers? Absolutely not! The goal was to create visibility and accountability, with top performers being proof that hitting KPIs was possible and what results they got in return.
Trending forecast
Next up we looked at where we we were forecasted to land AND BASED ON THE GAP define how many meetings needed to be booked for hitting quota. Because we were looking at a regional number in the MILLIONS (which can seem daunting) it was important to break this number down on an individual level so that reps could see the goal was possible. We considered factors like average deal size, Win rates, and Time to Close to define the goal for that week for reps in each segment.These first two points went pretty quickly.
Cross-functional updates
The third point was cross-functional updates across the go-to-market team consisting of Sales, Growth, Customer Success, and Product. Is this really important though?
Well I noticed that reps wanted to be enabled to sell so they were trying to get this information on their own from different teams and it was taking away precious selling time - not to mention that it was duplication of effort. We didn’t have a dedicated Enablement person at that time so I took it upon myself to bring these insights to the team and allow them to focus entirely on generating pipeline. On top this I made sure to emphasise how each of these updates would impact pipeline, win rates, and deal velocity to leave out the guesswork.
Feedback from the team
Once everyone was up to date I wanted to gather feedback on what was working so reps could learn from best practices and also raise awareness around what wasn’t working. This was crucial because tons of changes and developments were taking place internally and at times they caused processes to break. You’d think problems would get mentioned asap, huh? Initially it took weeks for issues to surface by which time the damage was already done so to get ahead of that I needed to know about friction sooner and then prioritise solving them that week.
Tip for Sales Managers: don’t be afraid to call on people individually to get momentum going.
If you’re working at a startup and the team doesn’t mention any blockers they’re either not trying hard enough or it’s just Monday and the coffee hasn’t kicked in yet.
Give recognition to top performers
By this time reps had a lot of info to digest and some may even be feeling the pressure so I needed to make sure the team was motivated to get going.
For this reason I made sure to end the meeting on a positive note by giving kudos where credit was due. If someone closed a deal (Air horn!), showed grit and ownership, or made an impact in other ways, they got a shoutout.
+1 Dad Joke Of The Week
Oh and I started these meetings with a dad joke to lighten the mood but either my jokes are terrible or the team could beat y’all in a poker face tournament any day. Please no comments!
How long should these meetings be?
My goal was to keep these meetings under 30 minutes but depending on the amount of updates internally and how much feedback the team had it could run up to an hour. Most Mondays we managed to keep it under 45 minutes.If I had to do it all over again I’d change some things that would bring the kickoff time down to 15 minutes. Stick around till the end to find out how!
Making it scale
Now I promised that this scales but so far this seems like a lot of work doesn’t it? Hear me out!
As a Sales Manager I was packed with meetings. Weekly forecast calls, bi-weekly management syncs, weekly pipeline reviews initially with each rep, later in segment groups, deal reviews, and the inputs needed for these overlapped a ton!
So what I did was prepare my detailed review of the week in one sitting and reused parts of it for each of these meetings.
This way I cut down prep time to about half.
To make this effortless I recommend capturing any update right away that impacts pipeline, win rates, or time to close. I personally saved slack updates with a single click and then reviewed them once a week on Sundays when I was preparing for the Monday kickoff. Standard dashboards from the CRM helped with the rest.
In addition to this I made the notes searchable so we could learn from our mistakes and successes in retrospect. But what’s the best way to do this?
Most people would create a new document for each meeting they run but unless you’re using a tool like Roam Research or Obsidian you will end up with siloed knowledge and waste a ton of time looking up information or suffer down the line trying to justify why you made certain decisions when your efforts fell short.
But this wasn’t about me.
First and foremost I needed the team to find information in seconds and to make this work I decided to log all notes on a single page.
The talking points got captured in a simple table - each row representing a new week. The result? Anytime you needed a refresher you could open this doc and find the info you’re looking for in 5 seconds with a simple search.
The last point was to have the team start using it and to reduce friction I bookmarked the page in the team Slack channel.
What I'd do differently in retrospect
But Viktor if this was working so well why would you change anything?
Well that’s the thing. These meetings were loooong at 45 minutes give or take and you could sense that the team was eager to get going instead of just sitting there.
Recently I talked to another Sales leader who runs Friday recap meetings with his regional team. They cover what results they got, what practices were working, and where they faced friction during the week. It’s a 30-minute wind down at 4pm before they log off for the weekend. And then it dawned on me! On Fridays the events of the week are still top of mind!
So am I proposing running Friday meetings instead of Monday kickoffs? No! You still need to create urgency and focus to get your team aligned after coming back from the weekend.
What I’d change is running a 15 minute kickoff meeting on Mondays and a 30 minute wind-down on Fridays.
On Mondays (I would still start with a dad joke because it’s in my nature) but then I would update the team on where we stand in the quarter and what we need to do to hit. Share departmental updates so information still comes to them, and then give a shoutout to the reps that made an impact last week.
What changes is the feedback section moves to Friday afternoons, and instead of collecting the Reps’ forecasts asynchronously I’d have them present their forecasts on the call. Maybe crack open a beer at the end to finish the week on a positive note too.
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