How To Ask workshop Case study

workshop connection

Posted on February 12, 2024 by Delyth Morgan (Del).

Workshops and team development has changed significantly over recent years. The working world as we know it has speeded up to a super fast pace with a seismic shift due to digital communication, AI and globalisation. Many of us are in a global market, whether we like it or not and the influences on our lives are governed by what appears in our feed and on our phone. That is controlled by mega social platforms via algorhythms, re-marketing and advertising. Information is fed to us and we're always busy sucking it in.

But what has this got to do with learning how to ask? Way more than you'd think...

As the pace of life picks up, all of this information demands our attention and the attention of those who we would like to engage with to support our efforts at work and play. So we have to keep up, be swift and nimble, capable and confident and ready to catch the attention of that one person who we want to ask something of. We'll only get one chance and a short 2 minutes of their time at best. If we're unprepared, unconfident, if we hestitate at all, that will be our chance gone.

An international organisation with development managers located across the world, engaged Let Me Out to help them upskill their team in a subject (or a theme) that was limiting their progress. That theme was How To Ask.

As an organisation looking to change lives through activity there are never enough resources to go around so they are faced with the need to ask often. There are also many reasons why they need to ask, be it funding, sponsorship, approval for a new programme, volunteer help, asking for support on a personal level or a pay review. They are all things that need asking and some of those asks are not easy at all.

Our workshop started with a 'walk and talk' session at a beautiful, inspiring location overlooking the ocean and walking through native bush. It's long been known that being immersed in nature is a great de-stresser and we wanted the group to feel at their most relaxed for the workshop ahead. But the walk came with some ice breaker challenges, all to do with practicing how to ask. The team were given two very specific questions to ask of one another as they walked in small groups of two or three. The walk might have been nice enough as it was but to make an effort to ask wellbeing questions allowed the connection and cameraderie between participants to grow. A deeper understanding and mutual empathy would help with the trickier tasks that lay ahead later in the workshop. It worked a treat!

The workshop itself was a 4 hour session, with breaks for morning tea and lunch. The location and venue, of primary importance for creating the right ambience for the work, was a beach style courtyard and low key restaurant. Private enough for the work to be unhindered, casual and creative enough to allow participants to relax into themselves and feel open to sharing their experiences. The last thing we wanted was a stuffy, corporate boardroom or sterile meeting space. This needed to feel welcoming and homely.

Arcadia courtyard Waiheke Island

The workshop began with a poll of opinions and experiences which we could use as a measure of where the sticking points were when it came to having to ask, whatever the ask was. Essentially we were gathering common feelings and emotions that come up often when asking was easy and when asking felt impossible.

Throughout the rest of the workshop we delved into many areas - systems, tips and tricks that would all help with developing the confidence to ask, the capability to ask and the insights on how to ask of different types of people. The rhythm of the workshop was quick, short delivery of the topic and as much time as possible spent on the participants practicing in small breakout groups with each other. PP - Purposeful Practice is the discipline of practicing a very specific skill that will lead to improvement. Development only happens when we repeat the practice over and over so that we can learn as we go, refine and retry. The result of PP is quick and visible improvement. Even if some of the practice feels hard (as most things we do for the first time do!), it gets easier and easier and before the participants know it, they're developing competency, skill and confidence beyond what they could have imagined. They also learn how to give and receive feedback which can be daunting at first but a brilliant tool for self development once you get over the fear of criticism and rejection.


The fear of asking from some more senior colleagues hinders progress
Some managers believe that people who are more senior than them are better than them
Overcoming self doubt is an important skill in learning how to ask
The fear of asking is a barrier for almost everyone
Understanding how to communicate with different types of people can significantly improve the success rate of the ask
Cultural and tradition can get in the way of asking
Body language plays an important part in gaining confidence when asking
Preparation is vital to take advantage of that brief opportunity that might present itself to ask a stakeholder - it may be an accidental ask when the moment presents itself so you must be ready
PP - Purposeful Practice - is what makes us better, quickly

"Thank you so much for our wonderful day. Everyone left having really enjoyed the workshop, with some great tools for dealing with potentially tricky conversations. I could feel the sense of empowerment everyone felt. The venue was perfect!

As you could see, the managers are a group of people who are really passionate about what they are doing to improve the lives of their communitiies, but who are often frustrated in their endeavours. I really feel that by practising the techniques you taught us, they will now be more confident in their dealings.

Personally, I also learnt a lot, with the workshop giving me a lot to think about in terms of being more assertive in my professional life."

Booking Manager.

If this feels like the type of workshop experience that could help your managers, please get in touch for a chat and no obligation quote.

"Change and growth go hand in hand. Confident people are happy to change" Delyth Morgan