Here are five key things we learnt from the conversation:

Personalities drive politics

The biggest takeaway from the conversation was how for better or worse, most political and policy arguments are refracted through the personality and characters of our most senior politicians and civil servants.  

Many of the political events of the last few years have been driven by a handful of people – many of whom view politics through their own ambitions or desire to do others down.

Theresa May did not understand the importance of communication

Perhaps not the biggest revelation, but reflecting how she dealt with both the media and her own party as Prime Minister, Shipman explained that part of Theresa May’s downfall was that she didn’t get the importance of the Prime Minister’s role as a lead communicator.  

Whether it was through stilted personal interactions with the media, or poor management of personal relations with senior cabinet ministers, May neglected her role as communicator-in-chief and failed to sell her vision of Brexit to the Conservatives or to the UK public – ultimately leading to her downfall.

Dominic Cummings a master strategist – but was too abrasive to succeed in office

Dominic Cummings is one of the most controversial advisors ever to work from 10 Downing Street – but he earned his place there, at least in the beginning.  

Shipman described him as being “touched by a form of genius” in his ruthless pursuit of a political vision and said that his work in Number 10 from summer 2019 until shortly after he helped Boris Johnson win a thumping parliamentary majority in the 2019 election may be one of the few times in recent years that politics has been done effectively in recent years. 

However, once settled in office his difficult to work with personality meant that he could not bring many key civil servants and politicians along with him, ultimately leading to his departure from frontline politics.

Boris Johnson did not fear Keir Starmer

One of the most intriguing insights from Shipman was his views on what lay behind Boris Johnson’s complacency on party-gate. 

Johnson simply did not fear a Starmer-led Labour Party, and believed that he would comfortably thrash him at the next general election. Why would he do anything but deny there was any wrong-doing and risk looking even slightly guilty, when there was no electoral impetus to do so?

Keir Starmer’s honeymoon will be short

A potential Labour Government needs to act fast if wants to be successful in Government. Shipman pointed to the fact that most enduring, positive legacies of recent Conservative governments – such as education reforms under the coalition – were all enacted in the first few months of office. 

Given the economic fundamentals and relative inexperience of Labour’s frontbench, events could take over even sooner – so a quick start will be essential to the success of an incoming government led by Keir Starmer. 

Our next In Conversation with: event will take place on 3 July with Labour MP for Birmingham Yardley, Jess Phillips. If you’d like to sign-up, place click here or email us at [email protected]