If you are a student of politics then you would be familiar with Niccolo Machiavelli’s book, The Prince. It’s one of the best books on diplomacy and avoiding “rookie” political mistakes.
In managing long sales cycles you should consider what strategy will help you keep the lines of communication open during the quiet periods. Every sale has periods where the customer is determining what to do.
Regular contact will keep the client motivated to progress the opportunity.
But what do you say to them?
You should always engage with them with a positive story – something unrelated to them. You may have sold to a competitor or a similar organisation to them. It’s a way to keep the discussion going without having to ask them, “so.. how is that proposal going?” (awkward silence on the other end!).
Find a legitimate and common interest that they are happy to discuss with you. Not sport! It has to be related to what you are selling. Industry related things are always good. If you are selling to HR professionals, you could invite them to a “thought leadership” breakfast or lunch to cover matters that relate to their organisation.
You are trying to add value to the relationship. This allows you to use back-channels to problem-solve any sales issues that might arise. You will find they will bring up the status of the opportunity before you do!
It’s dangerous to assume that organisations don’t change their mind. Always take the opportunity to confirm “where they are in their decision process”.
You are also trying to build a high degree of trust and credibility with the client. They will see you as the Trusted Advisor instead of just a regular sales person.In the end people buy from people they trust.

 A few years ago I was selling an e-learning platform to enterprise
and government clients in Queensland, Australia. One of my prospects was a
well-known not-for-profit business with 800 employees that provided telephone
counselling services.
My first meeting was with a consultant who was helping
their board improve their governance. He believed that our platform would
massively improve the way they inducted employees. The current CEO was expected
to leave in the next 6 months. The outgoing CEO was not a fan of online
learning, but my friend knew who the new CEO would be.
As I write this it feels
very Machiavellian! But our motivation was to make a real improvement to
this organisation. So I kept in touch with my contact for six months. Every few weeks when I made a sale to another client, I would feel on an amazing high, and
would give my friend to tell him the good news! This call was to let him know I
was still thinking about him and our opportunity we were working on. Other
organisations purchasing our product reinforced his decision to support me. And
there was a little pressure as well. “…so how long had we been talking
about this for?”
Eventually the new CEO started in her
role, and true to form she was very keen to modernise the governance of this
well-known not-for-profit. After a couple of months to settle in
my friend gave me a run-down of the entire board… the supporters, blockers
and neutrals. About 9 months after the initial meeting I made the board
presentation, the board was very supportive and it was then just a mechanical
process to get the contract across to have it signed.
In reflection I would never have known how to sell to that
organisation without the support of this consultant. This person did not hold authority but we shared the same values in wanting to help this not-for-profit. He gave me a window to its inner workings. Without that knowledge there would be no sale.
I worked with the client for a further six months and I saw the positive effect of the e-learning platform on the organisation. The CEO loved it and we received great feedback throughout the organisation.
In conclusion, like Machiavelli you need to pay close attention to alliances and those who can support you. This is the case – especially in long sales cycles.