Running a Sales Enablement Strategy

How are you thinking of a Sales Enablement strategy? While it seems simple the answer could be more complex than you think. The best sales organizations have credibility up and down the leadership tiers. If you lose that credibility then you lose the sellers.

And there is no faster way to do that then 1) waste everyone’s time with a BS training or 2) put a trainer up there who is just flat out bad. Now if you are like me then you want to run your own program. Some subjects are hands-on where you lead them while others are done through your enablement leader.

Now I have a disclaimer with my experience. I worked with a legend in the space named Chris Sargent aka the Godfather of Sales Enablement. He has trained close to 90% of sellers in the telecom space and needless to say he knows what he is doing. So I got the opportunity to be trained by him as a leader and saw how he rolled out a global program across hundreds of sellers.

The thing that I really noticed was how his themes tied together in his training. Each one built off the last one. This leads to my first suggestion

Build an Enablement Calendar

Start the process of building an enablement calendar. What subjects will you train on and why? How will you certify the reps? What frequency do you run it? When you start to line out your curriculum you’ll see how coherent it is. Here is a basic example:



Now how do I determine what subjects to train on? This is where your active involvement on calls is important. You’ll hear things that aren’t picked up on a report. Additionally, can you pull out themes in the QBRs you are conducting? 

One slide I loved was “What’s Working, What’s Not Working and What We Continue to Do.” The reps had a safe space to voice their frustration on what could be better…aka what enablement do we need.

Lastly, I would have a strong set of KPIs that you are looking at. Every VP is measured on average deal size, time to close and closing percentages. If you see one of these dipping then you need to study your revenue conversion true-ups to see what is lagging.

One thing you’ll see on this calendar is there is nothing for Dec. I believe that the end of the year is a sacred month for sales. Give as much time to sell and close to bring in revenue. 

Now how do you make sure the information is resonating? 

Certifications are Key

I’ll admit it. When I was in my earlier years of selling I absolutely hated being certified. I would try to come up with any reason NOT to do it. I can’t demo because the dog ate my demo account SORRY!

I started to switch that when I was able to take the learnings from the classroom and into real life. Once I got a taste of success then I was completely bought in. I also learned that these were the best opportunities to showcase my skills. It would only open doors for me later on.

As a leader I had to get a process together on how my certifications were going. The best practice that I settled on was to keep a scorecard of a reps performance. I could measure these quarter over quarter to see if they were maintaining a level of excellence. See here for an example:

It would also provide me meaningful feedback when we did mid-year reviews. I could call out specific items that they excelled in or needed a little more training on. Feedback is very hard to give out so you want to give it in a way that doesn’t step on anyone’s ego.

Constructive, Positive Feedback

I am naturally very competitive and always want to be the best. These would really come out when I was receiving feedback that I didn’t think was positive. It would just break my confidence and de-motivate me. 

This taught me an important lesson on how to give feedback so it’s heard. I do believe that everyone is giving their best effort and I don’t want to shame them. I lead with a positive, for example:

“Your transitions in your demo are some of the best I’ve seen but I would be mindful of your pace. You have a great message but it’s getting lost with how fast you are talking.”

To me that is a very constructive way of reinforcing what that rep is good at while letting them know where they have a vulnerability. It also beats saying “That was way too fast and it sounds like you don’t know what you are saying.”

Another example of constructive feedback is:

“You started off really strong out of the gates but it felt like you ran out of steam towards the end. What do you think?”

Rather than saying your demo sucked as it got to the end which would just discourage the rep. They may not know how to build a great story in a demo or they might be nervous because they want to do well. Offer them a life raft rather than being too brutally honest.

Now I know some of this appears to be common sense but you may be surprised that I have either 1) heard this feedback to my certifications or 2) witnessed it in certification feedback.

Measure Success

Remember at the end of the day you want to have your enablement be effective. You want to have buy-in from everyone that it’s worth their time. Make sure that your scores are staying consistently high but more importantly your Sales Org’s KPIs are improving.

Are deals moving more quickly? Is conversion rate increasing? Are deal sizes increasing? If you have green across the board here then congratulations… you have an effective enablement program. 

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