Sales Enablement Collective’s Slack channel recently hosted another expert “Ask Me Anything” (AMA) session, this time with Amanda Dossey, Senior Director of Sales Enablement at Keyfactor.

Amanda is an SEC Ambassador with over six years of experience across sales and revenue enablement, the perfect person to field the community’s sales onboarding questions and queries!

During the session, Amanda answered questions on:

And more!

Missed Amanda’s AMA session? Don’t worry, we’ve condensed all her answers right here. 👇

But if you want to catch the next session live, and even ask some questions of your own, join our Slack community and keep an eye on our #announcements channel!

Building a successful onboarding program

Q: “How do we go about building a successful onboarding program that actually works? It's overwhelming at times! 

“We have checklists that managers/employees follow and complete on their timelines, but I don't feel this is the most effective - but I also don't like to "babysit" the process. Do you have suggestions?”

A: Great question! When onboarding, I always feel the push/pull of what we can do in enablement versus how we can partner with sales/hiring managers. 

Before I build anything, I always start with my stakeholders. This is usually my manager and a variety of sales leaders (depending on the scope of your onboarding program). 

I do use a list, but I dig a little deeper to determine who does what and when. The accountability piece is so critical, otherwise, you definitely end up "babysitting." 

Before I meet with sales leaders, I break down the components of onboarding into what will be live and what can be done asynchronously. Asynchronous material can live in a sales enablement platform or even a shared drive. 

However, if you do have an enablement tool, it’s great because you can assign material and easily track completion! 

Live material will then be broken out into:

  • What enablement will cover
  • What sales leaders/hiring managers will cover
  • What other subject matter experts will cover 

I present this plan to all of the stakeholders and get everyone to agree on the plan.I also make sure that the sales manager's manager is involved (SVP of Sales, CRO, etc.). 

The good news is that you really only need to do this once. When everyone agrees on the framework, you can execute it as new hires begin to onboard. As things change and needs evolve, you can revisit the process above.

Once I meet with everyone and there is agreement on who does what, I book the live sessions for the new hire with each person. 

This ensures that everyone does what they agreed to do as part of the onboarding plan. 

It is a little manual, so this may not be possible depending on the size of your organization and/or the number of people on your team. 

If booking the live sessions isn't possible, you can work with the new hire to get meetings booked with their manager, etc. 

Meet with the rep once or twice weekly for a "check-in" and see what they have accomplished and where they are stuck. If they can't get the support they need, I will escalate it to management. 

I guarantee you that a rep will let you know what they need!

If you can establish a good cadence for assigning content, booking calendar meetings with SMEs and managers, and meeting with a new rep for quick touch-bases during the first few weeks/months, you will find that the need for following up lessens. 

Assuming accountability is in place, I have seen this work well. If you don't see accountability from either new hires or sales managers, that is a larger issue to discuss with sales leaders and your manager.

Which session format is best?

Q: “I'd like to know: Which format do you find more effective for your onboarding experience: instructor-led, in-person sessions akin to a classroom environment, virtual sessions, online modules, or other formats?”

A: I am a huge fan of all formats, depending on the situation! 

Process-type content that doesn't change much usually works well as pre-recorded content that reps can view on their own time. Generally, a lot of basic "101" content can be done this way.

I like live Q&A sessions to dig deeper into topics initially covered in pre-recorded content. Let the new hire ask questions and apply what they learned in a live dialogue. 

Specific selling skills, product enablement, etc. should usually be live. 

It's always great to be in person, but it isn’t always possible, given the remote world we live in. That being said, I have found that virtual meetings can be just as effective!

Whatever you decide to do, keep it fun and interesting. 

People don't want to sit in live meetings all day (major Zoom fatigue!), but they also don't want to sit and watch videos all day with no human interaction. 

Start out with basic material in a video format that gives them the flexibility to watch it when it makes sense for them. Do follow-up meetings to discuss what they reviewed, ask them what they think, and probe for questions. 

Set up live sessions with subject matter experts for more complex topics (think discovery strategy, sales skills, call shadowing, etc). 

There should be a good balance of material to learn and exposure to actual sales calls - this allows reps to apply what they are learning to actual customer scenarios.

Q: “How do you determine the right blend of on-demand vs virtual training? How much role-play and pitching do you do? Shadowing? We have a four-week onboarding program and the challenge is inputting too much information to the point where advisers become overloaded.”

A: That is the million-dollar onboarding question! 

When thinking about onboarding, I like to break it up. There is only so much material that an adult can consume at once, so I break onboarding into phases:

Phase One: I focus on knowledge to support a rep through discovery and into the proposal stage. The reality is that most reps aren't going to have deals progress past the proposal stage within the first few months. 

Some may, but generally speaking, it takes several months to ramp up fully. I usually spend the first month on this phase and really get a rep comfortable with discovery, product & pricing, and demo/working with solutions consultants.

Phase Two: I usually pick this up in months two or three; it just depends on your sales cycle. This phase will focus on the late-stage deal process (negotiations, procurement, etc.).

However you approach this, consider what a rep needs right now versus what can wait a few weeks/months. This gives the new rep time to digest the new material and also gives your subject matter experts some breathing room.

Choosing onboarding metrics

Q: “What metrics/KPIs do you use to measure your program effectiveness? What type of content are you delivering in your program that directly impacts those KPIs? And do those KPIs change?”

A: Great question. When you think about metrics and KPIs, look at it in two buckets:

  • Leading indicators: content completion, knowledge check/test scores, content engagement, rep satisfaction, etc.
  • Lagging indicators: time to first call, time to first deal closed, pipeline creation, quota attainment, etc.

Leading indicators can be tracked quickly, but they miss a critical part of the picture. Lagging indicators will likely take a while to track, but they can give you a much better understanding of overall onboarding effectiveness. 

However, leading indicators are great for adjusting strategy to ensure success by measuring a rep's will to put in the work and learn. If a rep isn't putting in the work, how will they be able to close a deal?

Lagging indicators can measure onboarding effectiveness, or sometimes even a rep's ability to learn.

If you see strong leading indicators but weak lagging indicators, it is a good idea to meet with the sales manager. 

It could mean adjusting some of the onboarding program, or sometimes it can indicate that a rep is struggling to do the job. Either way, it's an opportunity to dig in and find out what is going on.

Onboarding SDRs

Q: “I’d love to know how you deal with onboarding differences between SDRs and more advanced roles like Account Executives? How much of the content do you share vs separate between programs?”

When I think about SDR onboarding, I treat it like a junior sales role. When I break out onboarding into phases, I start with a "101" approach and then slowly build from there. 

So, an SDR and a sales rep will go through the same/similar material initially, but then they break into role-specific enablement. 

There are a lot of things that both reps and SDRs need to know, so there is quite a bit of overlap:

  • Marketplace/industry
  • Company messaging
  • Product & pricing
  • Discovery
  • Etc…

I start to see the paths separate when you look at tools (some tools will only be used by SDRs, some will only be used by reps, and some tools are used differently by each group), and the mid-to-late-stage sales stage process. 

But alignment between SDRs and sales reps is key, so I keep as much of their onboarding aligned as possible!

Q: “I'm developing our SDR onboarding right now and would love to hear your thoughts on the ideal timeframe for this specifically. 

“In my mind, once SDRs have a good understanding of the product and how we sell it, they can learn more on the job than in the classroom, so I have built a two-week program with regular check-ins for the first 30 days in the role, then the standard 60/90 day check-ins. 

“Does this sound about right or is a different approach better? And are there any non-negotiable things that you include every time for SDR training?”

A: I love that approach. I also usually spend about two weeks doing the foundational work while they listen to calls and shadow other SDRs. 

Then, by week three, they start to work a lot with their manager or mentor on actual calls. 

Regular check-ins are a great way for SDRs to ask questions outside of their manager. You can also get a sense of if their onboarding is comprehensive enough:

  • Are they getting the "real world" training from their manager? 
  • Is their foundational knowledge sticking?

New hires are much more likely to initially open up to enablement versus their managers when they first start a new role. 

In regards to non-negotiables, I always include industry background, competitive intelligence, company positioning/messaging, product, and objection handling.

Additionally, I like doing a variety of activities to apply and test concepts covered during onboarding. Whether it is onboarding or ongoing enablement, I build a foundation, reinforce concepts, provide examples of what good looks like, and build practical applications of the concepts.

Who needs to be involved in onboarding, and when?

Q: “What is your experience or opinion on best practice for getting frontline managers involved in their direct reports' onboarding? 

“How do we determine when they should weigh in, what is the value of doing so, while also ensuring they align to the onboarding program that has been designed (i.e. don't go off-script/freestyle!)"

A: I love this question, and I was just discussing this with one of our Sales VPs this week. 

The first step for me is always setting up expectations for both sides. With any new program, you will want to do an intake on any skills, concepts, etc., that reps will need in the next 30 days, 60 days, and 90 days. 

That has to come from them (or sales leaders, with frontline manager agreement) because:

  • A: It ensures alignment. If they share the need, they are more likely to help execute it.
  • B: There are many things that we, as enablement professionals, cannot teach as part of onboarding, such as live sales calls, region-specific knowledge, company-specific discovery processes, etc.

There will always be the core needs (think industry/competitive intelligence, sales tools, etc.), but frontline managers have to support the more “day-to-day” side. 

Once I have all the concepts, I map out a full onboarding ramp recommendation. Then, it goes back to the sales manager to review who does what

When there is agreement, I make sure all stakeholders are aware of who is doing what and when, including my manager, the sales manager’s manager, and anyone else that is aligned with sales onboarding. 

The good news is that, while this is usually a labor-intensive process, it only happens when you initially build a program. 

I will do check-ins and content/program updates with managers one or two times per year, but that is a much faster process.

When a rep is onboarded, I think of myself as the “tour guide”. I kick off a rep’s experience, walk through the program, and help set up their initial meetings. The new rep should also be aware of who does what. 

The SEC onboarding playbook - download it today!
We worked with our partners at Second Nature and other expert onboarding professionals to build this playbook. Download and elevate your processes today.

Outside of any enablement-led onboarding, I meet with new reps one or two times a week to do a check-in and see where they are blocked. 

This is usually when a rep will tell you if they haven’t been able to connect with their manager, and that is then my opportunity to go to the manager directly and ask them how I can support them. 

It’s in the best interest of the manager to ensure a rep is properly onboarded so they can start closing deals! 

And while it rarely happens, if you can’t get anything done with the frontline manager and you get blocked, you can escalate it to your other stakeholders.

Q: How hands on are you during the actual onboarding? Do you run most of the training, or are you more of a quarterback connecting new hires with their training, content, meetings, etc.?

A: I like a mix of asynchronous training that reps can do on their own, live training with me, live training with subject matter experts, and live training with frontline managers. 

I make sure that the rep is completing the various steps and I will do a few live training sessions, but a lot of it is connecting the new hire to the right SMEs!

Finding more AMAs and sales enablement content

First of all, another big thank you to Amanda for taking the time to answer the sales enablement community’s questions. 

If you want to ask a question of your own next time we host one of our regular "Ask Me Anything" sessions, all you have to do is join our free Slack community. 

You’ll join thousands of your sales enablement peers in a space where you can network, share content, ask questions, and stay up to date with all the latest in the space. 

What’s not to like? Join the community for free today.