In today’s selling environment, there’s no such thing as a “simple” sale anymore. Everything is becoming more complex — more stakeholders, higher risks, longer timelines.
In this post, we dive into a recent conversation between sales pros Mark Hunter and Meridith Elliott Powell as they unpack what really works in closing complex deals.
What Makes a Sale Complex?
Complex sales are defined by a few common traits:
- Higher-than-average investment
- Multiple decision-makers with different priorities
- Solutions that are customized or outside the client’s standard scope
These deals often stall because the customer fears making the wrong move, especially if they’ve had bad experiences in the past. Risk aversion is real — and it’s paralyzing.
The Default Competitor? No Decision.
Sometimes your biggest competitor isn’t another vendor — it’s indecision. When things feel too risky or too complicated, buyers often choose to do nothing. Salespeople must recognize this early and work to remove friction, not just from the product or service, but from the process itself.
Strategy #1: Patience Is More Than a Virtue
A key takeaway from both hosts? Slow it down. You don’t control when a complex sale closes — the customer does. Patience is not just strategic; it’s essential. Rushing the deal only increases the chance it will fall apart before or after signing.
Strategy #2: Create Proof and Confidence
Proof of concept (POC) matters. Buyers often need reassurance that your solution will actually work — especially when it’s something new or customized. Be ready to show success stories or offer a small trial if appropriate. When buyers are unsure, “no decision” becomes the safe choice.
Know Your Players — and Their Real Roles
One of the most nuanced challenges in a complex sale is knowing who’s who. The economic buyer isn’t always the end user, and the person talking the most may be a hidden saboteur. Build maps of the decision-making ecosystem and be aware of internal politics.
Strategy #3: Prioritize Your Time
Before diving into a complex deal, ask yourself: Is this prospect truly in your ideal customer profile (ICP)? Do they have a real need — and is it a top priority? Complex sales demand major investment, so don’t spend time where there’s no urgency.
Strategy #4: Set Clear Expectations
False expectations kill deals. If the buyer expects something you can’t deliver, the implementation will break down — even if the contract is signed. Vet the opportunity thoroughly and align on expectations up front.
Influencing Factors That Matter Most
Mark and Meridith shared key influencers that determine whether a complex sale succeeds:
- Is the problem tied to a critical priority?
- What’s the financial impact?
- How does it align with the company’s strategic direction?
And yes — read the 10-K. If you haven’t done your research, you’re not ready to sell.
Strategy #5: Customize for Their Driving Factor
Every deal has one major driver. Maybe it’s speed. Maybe it’s ROI. Maybe it’s internal promotion. Figure out what truly matters to the buyer and align your pitch with that. The more personalized, the more effective.
Strategy #6: Ask the Hard Questions
Don’t be afraid to ask: Who else are you considering? What’s the decision-making timeline? What’s the internal process for purchases like this? These questions clarify not only where you stand, but how to move forward.
LinkedIn and the Power of Multi-Threading
Bryn Tillman makes a great point — success in complex sales means engaging the entire decision-making ecosystem. LinkedIn is your friend. Use it to identify and connect with stakeholders across functions. Influence needs to happen before the decision moment.
Strategy #7: Bring a Team to Meet a Team
Selling alone against a roomful of decision-makers is a losing game. Bring in your own experts — product specialists, implementation leads, customer success. Match the client’s complexity with your own depth.
Strategy #8: Slow Down to Speed Up
When you stop pushing and start being present, you build trust. People don’t buy when they feel pressured. Slowing down shows confidence — and gives your buyer space to move at their pace.
Question of the Week: How to Break Through a Stalled Deal?
Sina from Tokyo asked how to push a deal that’s stuck despite strong conversations. The answer? Dig deeper into each stakeholder’s role and motivator. Develop personal relationships, not just professional touchpoints. And always align with urgency.
Strategy #9: Find Your Internal Champion
A coach supports from the sideline. A champion gets in the game. You need both. Champions are internal advocates who can open doors, get meetings, and push for decisions. Find them early, and empower them to help you win.
Strategy #10: Sell the Urgency
If a deal is stalled, it’s because the buyer doesn’t see the cost of inaction. Your job? Help them see it. Be bold. One example shared involved calling out a company for trying (and failing) to train leaders for three years — a challenge that finally moved the needle.
Final Thought: Emotion Drives Decisions
Even in complex B2B sales, people buy emotionally first — and justify logically later. Don’t underestimate the emotional component, especially when multiple influencers are involved. Understand it, speak to it, and sell to it.
Ready to close more complex sales? Slow down. Ask better questions. Map the decision-making team. And above all — never forget that even the most complex deals come down to trust, clarity, and value.
Lightning Round: Top 10 Ways to Build Your Personal Brand
Question: Sina from Tokyo, Japan asks, “I work in the financial services industry, and expanding my portfolio is a long sales cycle – feels like these days it is getting longer. I am doing a great job of getting the meetings, and connecting with decision-makers. I am even having good conversations, but not quite getting the decision-maker to make decisions—any ideas would be appreciated.”
Book: Secrets of Closing The Deal by Zig Ziglar