How To Be ‘The Cool Boss’ While Still Retaining Respect


Many small business owners know just how hard it can be working under someone with unreasonable expectations, or a prickly demeanor. However, just like parenting, being overfriendly and oversocial in the office environment as a manager can be strange. Both the UK and the US have quite literally made two excellent sitcoms revealing the absurd humor that can often come with this. 

Does that mean you need to be a stone-faced tyrant in order to fully fit into the role of office manager? That we need to keep our upper lip stiff and our mind towards our work and our profits only? Of course not. That can lead you to become a Scrooge-like character. So where is the middle ground? Is it actually possible to be ‘the cool boss’ while still retaining the respect of your employees? How are you supposed to balance this? And, moreover, how can you do anything but force it? 

We would say that you can achieve this. To answer the other questions, we might need to explore below:

Give Meaningful Praise

The first issue that many wannabe ‘cool bosses’ can make is continually complementing their staff, even if they’re only committing to the baseline responsibilities outlined in their contract. These bosses can often have experience of being under-appreciated at a firm, knowing just how tiring that can be. But the issue here is that an over-reliance on unsubstantiated praise only leaves your staff feeling somewhat tepid in their reaction. They know they don’t deserve it, and your praise is just a small and lazy motivational sentiment. Keeping your praise for when it actually matters. Not only that, explain why someone did a good job, and show the others on the team why that is. When you back this up, and give it infrequently – it actually means something. Not only does this encourage your team to try harder, but it can also give your words more weight.

Give Meaningful Discipline

You are running a business, not a social club when all is said and done. It’s important to understand this. If a boss is too lenient, they can be taken advantage of. Unscheduled breaks, coming in late, leaving early, all of this can start to foster in the behaviors of staff who feel unchallenged, even those who might otherwise be well behaved and well meaning individuals.

Discipline your staff – fairly, but uncompromisingly. Let them know the standards you expect. If they conform to that, then you can be friendly of course. But always keep that strong fundamental need in mind. Your staff will understand.

Care For Them

Set up your office culture and employment policies to take care of your staff. Utilise occupational healthcare services to ensure your people are well encouraged and taken care of, and that a positive standard is set. This can also ensure that drug testing is performed to help your staff know you only select those who can be fully trusted, thus improving the office atmosphere. If you can do this, then caring for your goals can be a valid means forward.

With this advice, we hope you’ll be better able to remain the ‘cool boss’ while still retaining success.


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