We often hear about the need to strike up the right conversation with a senior leader. Using the right language, questionning technique and business tone is highest on the list of most sales organisations today as they develop their winning techniques and go to market strategies. And quite right too, as the person across the table from us is also seeking to have the right level of conversation with any partner hoping to supply goods and services to them. As we are realising with accelerating clarity that the successful sale has to be able to consider not just a single threaded conversation like “what is it that you want or need” but now a more multi-threaded one, the challenges is equipping ourselves with the skill to be able to engage and sustain three conversations simultaneously with the stakeholder we are going to meet. Remember that killer ( you must ask this one ) question? “So what keeps you awake at night?”. I recall asking this very same question of very senior CIO of a very very large corporate when given the opportunity to ask just one question. And the reply? “Nothing.” Nothing kept this particular CIO awake at night because his skill was in being able to keep these three balls in perpetual motion through his leadership style. That was it. Sure he admitted there were specific challenges that concerned him, but as the true leader he was, the team he had built did a lot of the sleepless nights for him. In fact, the CIO turned the question back on me and wondered what would keep me awake at night if I were to be fortunate enought to provide services to his organisation. Ouch. A very neat back hander to suggest that in fact it would be I that would not be getting any sleep. Because to deal with his organisation with the depth of experience and foresight present within his management structure and beyond, would put me under the pressure sufficiently to affect my sleep patterns! You see these C levels thought leaders and human agents of change are masters of keeping three conversations going on at the same time in their heads. Translated to meaning they build successfuL IT organisations and partner relationships specifically to ensure these three conversations are constantly being discussed, reflected upon and challenged. And the three conversations? (1) How do I go about steadying and stabilising the back office, whilst (2) transforming the experiences for my front office customers, (3) while at the same time creating the digital platforms to allow the thought leadership ideas of my own and my peers to turn into true competitive advantage for my organization and shareholders. The mashing together of old and new, support and service, and analog and digital form the basis of these conversations that reach deep inside the organisation, and require a certain level of skill to ensure that outcomes are realised. When embarking on a conversation with such leaders the tone and range of the language therefore has to be wide and far reaching. Expecting a successful outcome by just following one of the conversation threads may ultimately fall short, as the leader is considering your pitch against the other two conversations going around in their heads. You see these conversations are instrincally linked and the impact of decisions in one of the threads will affect the other, so the juggling of the three conversations drive the need to engage in a more balanced conversation to ensure your questionning tests and challenges the leader. Yes tests and challenges are the key words here. I have never met a senior leader who doesnt expect ( nor flourishes ) on being tested and challenged. The last thing they want is someone in front of them nodding and agreeing passively in the vain hope that an order will be fortcoming. The challenger sale is absolutely right. Earning the respect and opportunity to put forward your own thoughts and vision to how you can help in any of the three conversations is where you need to get to. The senior leader expects this and will respect your position more if you are prepared to engage proactively. Planning your approach knowing that there are in fact three conversation threads that you may need to be able to juggle yourself is therefore, the golden opportunity for the sales organisation. Gone are the days where the senior leader is going to say to you “what I need is XYZ”. Gone are the days where the conversation will start and finish with “So go and away and give me your best price for ABC”. Discussions around “demonstrate to me your USPs” are fast fading away. In their place the conversation is now “show me how you have understood my challenges and opportunities in one or all of my conversation threads and come back to me with a specific plan to help me move my organisation forward”. And its a really tough thing to do because not only has the landscape for our questioning been made more complex because of the shifting sands of choice for technology ( cloud, ,mobile, social and big data ), but that behind the physical persona of the stakeholder in front of us exists similar mini-me leaders representing the execution arm of the CIO’s inner circle. Whether it is the CIO’s office, leadership team, Number Two or management layer, being able to take your propositions in any of the three conversational threads forward requires you to be able to maintain and drive forward your offers and propositions deeper into the leadership team – potentially all at the same time. A lot harder and you will need your own leadership team to support you. And this is key. To keep your own ‘three balls’ being juggled at the same time means you cannot do it on your own. You need the proverbial three pairs of hands and that your team has to be like minded and similarly driven to hold a positive and challenging conversation based on skill, experience and demonstrable capability. I dont know whether its a littl exercise that we can all undertake as we prepare to meet senior leaders, but I am pretty sure I wish I had know this before I opened my mouth that day with that senior CIO. Firstly, I know my conversation would have lasted a hell of a lot longer, and I am pretty sure I would have engaged in a more intellectual and challenging conversation rather than discussing sleeping patterns of the exceptional thought leader sitting in front of me! Now this may mean we spend more time being ‘awake at night’ as we build our language and techniques to prepare for engagements in the future, but it will be well rewarded as we ensure that the leader you hope to service ‘gets plenty of sleep’ as you demonstrate your true value proposition to their organisation. Brummie.