5 Mins Read

How To Take The Fear Out of Pipeline Discussions With Sales Leaders

Brandon Fluharty |

Brandon Fluharty |


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⚡️ Today’s level up ⚡️

Today’s edition focuses on helping you remove the fear from pipeline discussions with your sales leaders.

Let’s go!

Read time: <5 minutes

If you missed last week, read it here.


I loathed 1:1 pipeline discussions with my leaders

Even when I was on top as a perennial producer, I feared 1:1 discussions with sales leaders.

They always felt like “gotcha” moments. Leaders were working extra hard to expose me. I thought they wanted to show me that my strategy was flawed, needed to be scrapped, and that they knew better.

In hindsight, I now know this thinking was utterly ridiculous.

My leaders simply tried to find gaps where I couldn’t see them. Identify blocks that could be removed. Think through risks that could stall or kill a deal.

I’ve been thinking about this a lot lately, as one of my 1:1 coaching clients has been gracious enough to share his recent recordings with his sales leaders.

Like me, these meetings have caused him a lot of unnecessary stress and anxiety and I want to use this edition to help reframe your thinking and approach to these meetings in case they are a source of anxiety, too.

The sales autonomy hierarchy

Many of us entered sales because it’s one of the most freeing roles in the corporate space.

If you deliver results, you’re generally left alone to do your own thing. But that’s highly simplistic, so I wanted to create a 5-level hierarchy to help you identify where you might sit on it based on what’s happening within your own business.

Level 5: Meeting or surpassing quota

– When you’re 100%+ to quota, generally, you’re left entirely alone, and the tone and focus are of reverence for the stellar work you’re doing and gauging your satisfaction level.

– You’ll hear things like, “What do you need?” “How are you feeling?” “What is next year looking like for you?”

– At this level, leaders’ jobs are to ensure you’re happy, committed to helping you build a legacy at the org, and able to sustain a high win rate with higher demands.

Level 4: Generating revenue

– When you’re consistently generating revenue each quarter but not quite hitting or surpassing your target, the tone and focus is about diving deeper into strategy – the minor tweaks or levers that can be pulled in your accounts, like understanding how leaders can help assist in removing blocks or de-risking an opportunity.

– You’ll get questions like, “What’s the biggest risk for this opportunity?” “How can we expand this deal?”

– At this level, it’s about executing a sound strategy and utilizing more sophisticated tactics to unclog the blockers, expand on the deal size, and accelerate deal cycles.

Level 3: Generating pipeline (qualified opportunities)

– When you’re consistently generating pipeline but not generating revenue, the tone and focus are around elevating your business acumen and value creation (to identify urgency, level up inside their org, multithread and create multiple champions, and effective positioning against the competition or status quo)

– You’ll get questions like, “Who is/are your champions?” “When are they looking to implement a new solution?” “Are there any detractors?” “What is your position/POV going to be?”

– At this level, it’s about helping you to deliver more impact with what you have vs focusing on new activity.

Level 2: Generating activity (discovery meetings)

– When you’re busy setting and/or running meetings, but no meaningful opportunities are being created or progressed, the tone and focus center around improving your communication skills or ensuring you have a deeper understanding of the company’s solution or how to identify or solve your prospects’ problems.

– You’ll hear things like, “What are they trying to solve for?” Who are you engaged with in that account?” “What’s the next step, and when will it occur?”

– At this level, it’s about helping you turn meetings into more predictable outcomes and timelines.

Level 1: No visible contribution (danger zone)

– If you’re outside of your onboarding period and you don’t yet have a proven track record of closing business at the company, and there is nothing documented on how you have been spending your time, then your job is at risk, and the tone is stark.

– You’ll hear things like, “We need to see improvements.” “You’re trending behind what we normally see with AEs at this stage.” “I want to see a plan put in place for our next 1:1.”

– At this level, it’s about understanding if an investment in you or a new hire is more fruitful.

Identifying where you sit on this hierarchy, allows you to be radically transparent with yourself and the process you need to be undertaking to move up a level.

This self-categorization allows you to enter 1:1s with sales leaders with less trepidation and more emotional control so you can keep your focus on making meaningful progress on your accounts.

Thinking how a leader thinks

Verbatim, here’s a snippet of the discussion my client, an Enterprise AE at a public SaaS company, had with one of his leaders (two levels above him, who leads sales for a specific product within the larger parent company).

The leader explained it this way to my client, whose pipeline for Q4 and Q1 are a bit light:

There is no value in activity for activity’s sake. I work backward from QOs (Qualified Opportunities). So if you’re hitting your QO target, I don’t look at anything else.

If you’re not meeting your QO targets, I look at how many discovery meetings you run each week. If you’re not having 2 to 3 discovery meetings per week,I look at how many emails and activities you send out.

At the end of the day, activity and meetings are leading indicators for pipeline generation – and all I care about is generating pipeline.

So, however you get there, however many tries it takes, isn’t significant; it’s about getting there. And then, once you generate pipeline, it’s about how you’re actively managing that pipeline.

As leaders, we don’t get into the weeds every day, so I have to look at dashboards, and then I use those dashboards to make strategic decisions on predicting revenue, and go a level deeper to maintain a pulse on whether the qualified opportunities are progressing.

One of the things I like to look at in Gong, across teams, is pipeline from a standpoint of all deals in play (from a future date), and then I look at the activity and when the next call is scheduled. Having a call scheduled gives me a signal that we have an active opportunity.”

Maybe this sounds familiar or is all new insight for you, but it should give you a glimpse of how an actual leader at a public tech company in charge of many millions in ARR thinks.

Leaders are not trying to throw out “gotchas.” They are way too time-strapped for that. They seek individual contributors who think strategically and proactively about their account lists and opportunities.

They have a significant number on their head. They are looking to you, as the person closest to the customer, to defend why this deal will happen and when it will happen when you say it will so they can challenge that assumption with strategic questions that will identify potential weaknesses in the plan to offer a remedy.

Ultimately, it comes down to testing what works and what does not. The company doesn’t have all of the answers for you, but a good leader is looking for sellers to make intelligent decisions and apply effort to their account lists until they find success, then refine and repeat that success.

A golden rule I recommend is always trying to put yourself in the shoes of whoever you’re engaged with.

– How do they think?

– What do they care about?

– How can you tailor the discussion to maximize benefit for both sides?

Once you have a clearer picture of how your leader thinks, you can come into the meeting with a focused agenda (supported by a narrative plan) that accurately addresses the state of your business and invite them into a collaboration to improve it.

That’s a wrap. See you next week!


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