If your B2B deals keep stalling after a great start, you're likely stuck in the sales middle game—here’s how to navigate it like a pro.
This is the second article on approaching sales with a chess mindset. We already discussed the importance of laying the groundwork of your strategy with your opening. Now, we’ll look at the middle game.
Navigating the B2B Sales Middle Game: How to Stay in Control When the Process Gets Messy
In professional sales, the middle game is often difficult. You start the sales conversation with high hopes. You’ve set up your strategy, and the game is underway. Now, you’re running into obstacles. Your main contact, who gave you time early in the conversation, now has no time for you. They don’t seem interested in continuing the conversation. No one returns your voicemails; no one opens your emails, much less replies to them. You have done everything the experts suggest you do, but nothing works.
You schedule a meeting, doing your best to get all the decision-makers and stakeholders in a room together to align the client’s needs. They are facing a rare decision with high stakes. You know they are worried about getting it right the first time. You manage to book the meeting, but two of the senior leaders leave the conference room after 20 minutes to meet with one of their own clients. Things stall again.
In chess, the middle game is where most of the strategy plays out. An expert player knows that this is an unpredictable time during a match. In the opening, players initiate their strategy and analyze their opponent’s game. To do this, they draw on established variations that can often be memorized. In high-level chess, openings are generally grounded in theory, which makes them somewhat easy to evaluate.
In the middle game, play is more complex. Players must protect their king while keeping their other pieces in play. This takes a lot of orchestration. Chess masters make sure their most valuable pieces are mobile and ready to attack if an opening presents itself. Depending on a player’s strategy, it might make sense to sacrifice pawns to open up the board so rooks, bishops, and queens can move freely; however, they must be careful not to offer the same advantage to their opponent.
In the sales middle game, as you struggle to regain momentum, a number of contacts are uncertain about how making this change will impact their business. They seem to wonder if it’s not better to stick with the status quo, even though it’s not working for them. Then, the client makes a strange move. One of the main contacts tells you that he is the only person you are allowed to talk to, even though you already have meetings scheduled with his colleagues. You decide to keep all appointments on your calendar, but you are unsure of your next move.
Two days later the main contact tells you that the client company has downgraded the initiative you have been working on. It is no longer a priority. The client tries to tell you that it will be back on the agenda after the client finishes pursuing a new shiny opportunity. You sit down with your sales manager to see how your pipeline is growing. As you’ve focused your time on pursuing this stalled deal, your prospects have thinned. Your manager tells you that you need to pump up the opportunities in your pipeline, mumbling something about being sure you will convert them before the quarter ends.
Meanwhile, you still have hope for the deal your client downgraded. You try to lead them to consensus, but it is easy as herding cats—not house cats, the feral kind. As you are doing your best, the client’s two senior VPs ask you to share your ideas at that point. Then, they decide not to greenlight the initiative.
Like in chess, the sales middle game does not necessarily reach the endgame. All kinds of things go wrong, leading to a stalemate. For a salesperson, this is the same as a loss.
The strategy in the middle is mostly about persisting. You must remind your champion the better results they need, and why change is the only way to get there. Like in chess, time is important. You must spend time with the decision-makers and their stakeholders, but you cannot rush things. Take a long view of your strategy, and work day by day to strengthen your position.
Instead of seeing your contacts as your opponents, team up with some of them to gain support for your initiative. One sales champion can capture their colleagues, helping you develop a material advantage and build consensus. Instead of looking at the end result, focus on the individual moves you need to get there. Talk to your contacts to learn about their specific needs, priorities, and concerns. Connect with them on an individual level to earn their trust while you strengthen your position.
To build your case, make sure that every move develops your strategy. Your middle game should be a natural continuation of your opening. Once you’ve gotten your contacts’ attention, you need to gain their buy-in. Working through a series of moves, instead of relying on a single meeting or contact will help you educate your client about the importance of change. This approach can help you transition from the middle game to the end game.
No matter how difficult it is, focus on the board and keep your pieces in play through the messy middle game.
