Andrew Brodie also said much of the estate is “dilapidated” and that technological advancement in equipment, fleet and ICT have “too often not been made.”
He said in the report that fire stations at Northallerton, Scarborough and Richmond are “not fit for purpose.”
The report has been published by North Yorkshire Police, Fire and Crime Commissioner Julia Mulligan.
It follows the change in governance from the fire Authority to the Police, Fire and Crime Commissioner in November last year.
Mr Brodie said: “My first 100 days has been a fascinating and eye-opening time, and I have enjoyed every minute.
“I’m part of a fantastic team and workforce, we all want the best for North Yorkshire.
“There are though things which need to change, and I have made that clear in my report.
“I have also set out a vision of what I know the dedicated and professional staff can achieve.”
Mr Brodie wrote: “We suffer from chronic long-term under-investment and some long-standing cultural challenges.
“Much of the estate is dilapidated, too many workplaces are uninspiring.
“Technological advancements in equipment, fleet and ICT have too often not been made.
“Mistrust exists between layers of the organisation and this stifles initiative.”
Mr Brodie added in the report: “Too much of our estate is dilapidated. Buildings are crumbling, uncomfortable and uninspiring.
“They are not welcoming for public use and facilities are inappropriate for a diverse workforce or visitors.
“Stations such as Northallerton, Scarborough and Richmond are not fit for purpose or appropriate to share with other organisations.
Mr Brodie said in the report that parts of the North Yorkshire Fire Service workforce are not diverse enough.
He said: “Most starkly the low numbers of firefighters who are women and the consequent dearth of women in senior firefighter roles.”
Mr Brodie said in the report that new fire engines and equipment are high quality, modern and fit for purpose, but added: “However, older fire engines are not fitted with modern technology such as passive and active safety features or electronic pump controls.
"We have not embraced modern firefighting techniques that are in place in other fire and rescues services.
“In future we’ll use the more up to date technology that is commonplace in other services, expanding our use of foam systems and considering use of high pressure misting systems.”
North Yorkshire Police, Fire and Crime Commissioner Julia Mulligan said it is “hard to disagree” with Andrew Brodie’s views on the chronic underinvestment in the county’s fire service.
Ms Mulligan added: “I will be publishing the first Fire and Rescue Plan for North Yorkshire soon, which will set the priorities for the next two years.
“Thank you to all those who took part in the consultation, which has helped shape and focus the plan.
“I look forward to working with Andrew to put that plan into action and setting a strong foundation for a bright future for the fire and rescue service.”